Synthesis of new chiral 2,2′-bipyridine ligands and their application in Copper-catalyzed asymmetric allylic oxidation and cyclopropanation

Journal of Organic Chemistry

Volumn 68, Issue 12, 2003, Pages 4727-4742

  Malkov, Andrei V ^a   Pernazza, Daniele ^a,c   Bell, Mark ^a   Bella, Marco ^a,d   Massa, Antonio ^a,e   Teplý, Filip ^a,f   Meghani, Premji ^b   Kočovský, Pavel ^a  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

^c CARDIFF UNIVERSITY   (United Kingdom)

^d SCRIPPS RESEARCH INSTITUTE   (United States)

^e UNIVERSITY OF SALERNO   (Italy)

^f CHARLES UNIVERSITY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COMPLEXATION; COPPER; OXIDATION; SYNTHESIS (CHEMICAL);

CHIRAL MOIETIES;

ORGANIC COMPOUNDS;

2 CARENE; 2,2' BIPYRIDINE; 2,2' BIPYRIDINE LIGAND; 3 CARENE; ALKENE; BETA PINENE; BISTEROID; COPPER; DEHYDROPREGNENOLONE ACETATE; ISOPRENOID; PHENYLHYDRAZINE; PINENE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CYCLOPROPANATION; DIASTEREOISOMER; ENANTIOMER; OXIDATION; REACTION ANALYSIS; ROOM TEMPERATURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037603215     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034179i     Document Type: Article

References (202)

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19. (a) Hayoz, P.; von Zelewsky, A. Tetrahedron Lett. 1992, 33, 5165. (b) Fletcher, N. C.; Keene, F. R.; Ziegler, M.; Stoeckli-Evans, H.; Viebrock, H.; von Zelewsky, A. Helv. Chim. Acta 1996, 79, 1192. (c) Gianini, M.; von Zelewsky, A. Synthesis 1996, 702. (d) Mamula, O.; von Zelewsky, A.; Bark, T.; Bernardinelli, G. Angew. Chem., Int. Ed. 1999, 38, 2945. (e) Lötscher, D.; Rupprecht, S.; Stoeckli-Evans, H.; von Zelewsky, A. Tetrahedron: Asymmetry 2000, 11, 4341. (f) Kolp, B.; Abeln, D.; Stoeckli-Evans, H.; von Zelewsky, A. Eur. J. Inorg. Chem. 2001, 1207. (g) Lötscher, D.; Rupprecht, S.; Collomb, P.; Belser, P.; Viebrock, H.; von Zelewsky, A.; Burger, P. Inorg. Chem. 2001, 40, 5675. For overviews on the synthesis and application of 2,2′-bipyridines, see: (h) Knof, U.; von Zelewsky, A. Angew. Chem., Int. Ed. 1999, 38, 303. (i) Chelucci, G.; Thummel, R. P. Chem. Rev. 2002, 102, 3129.
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21. (a) Hayoz, P.; von Zelewsky, A. Tetrahedron Lett. 1992, 33, 5165. (b) Fletcher, N. C.; Keene, F. R.; Ziegler, M.; Stoeckli-Evans, H.; Viebrock, H.; von Zelewsky, A. Helv. Chim. Acta 1996, 79, 1192. (c) Gianini, M.; von Zelewsky, A. Synthesis 1996, 702. (d) Mamula, O.; von Zelewsky, A.; Bark, T.; Bernardinelli, G. Angew. Chem., Int. Ed. 1999, 38, 2945. (e) Lötscher, D.; Rupprecht, S.; Stoeckli-Evans, H.; von Zelewsky, A. Tetrahedron: Asymmetry 2000, 11, 4341. (f) Kolp, B.; Abeln, D.; Stoeckli-Evans, H.; von Zelewsky, A. Eur. J. Inorg. Chem. 2001, 1207. (g) Lötscher, D.; Rupprecht, S.; Collomb, P.; Belser, P.; Viebrock, H.; von Zelewsky, A.; Burger, P. Inorg. Chem. 2001, 40, 5675. For overviews on the synthesis and application of 2,2′-bipyridines, see: (h) Knof, U.; von Zelewsky, A. Angew. Chem., Int. Ed. 1999, 38, 303. (i) Chelucci, G.; Thummel, R. P. Chem. Rev. 2002, 102, 3129.
22. (a) Hayoz, P.; von Zelewsky, A. Tetrahedron Lett. 1992, 33, 5165. (b) Fletcher, N. C.; Keene, F. R.; Ziegler, M.; Stoeckli-Evans, H.; Viebrock, H.; von Zelewsky, A. Helv. Chim. Acta 1996, 79, 1192. (c) Gianini, M.; von Zelewsky, A. Synthesis 1996, 702. (d) Mamula, O.; von Zelewsky, A.; Bark, T.; Bernardinelli, G. Angew. Chem., Int. Ed. 1999, 38, 2945. (e) Lötscher, D.; Rupprecht, S.; Stoeckli-Evans, H.; von Zelewsky, A. Tetrahedron: Asymmetry 2000, 11, 4341. (f) Kolp, B.; Abeln, D.; Stoeckli-Evans, H.; von Zelewsky, A. Eur. J. Inorg. Chem. 2001, 1207. (g) Lötscher, D.; Rupprecht, S.; Collomb, P.; Belser, P.; Viebrock, H.; von Zelewsky, A.; Burger, P. Inorg. Chem. 2001, 40, 5675. For overviews on the synthesis and application of 2,2′-bipyridines, see: (h) Knof, U.; von Zelewsky, A. Angew. Chem., Int. Ed. 1999, 38, 303. (i) Chelucci, G.; Thummel, R. P. Chem. Rev. 2002, 102, 3129.
23. (a) Hayoz, P.; von Zelewsky, A. Tetrahedron Lett. 1992, 33, 5165. (b) Fletcher, N. C.; Keene, F. R.; Ziegler, M.; Stoeckli-Evans, H.; Viebrock, H.; von Zelewsky, A. Helv. Chim. Acta 1996, 79, 1192. (c) Gianini, M.; von Zelewsky, A. Synthesis 1996, 702. (d) Mamula, O.; von Zelewsky, A.; Bark, T.; Bernardinelli, G. Angew. Chem., Int. Ed. 1999, 38, 2945. (e) Lötscher, D.; Rupprecht, S.; Stoeckli-Evans, H.; von Zelewsky, A. Tetrahedron: Asymmetry 2000, 11, 4341. (f) Kolp, B.; Abeln, D.; Stoeckli-Evans, H.; von Zelewsky, A. Eur. J. Inorg. Chem. 2001, 1207. (g) Lötscher, D.; Rupprecht, S.; Collomb, P.; Belser, P.; Viebrock, H.; von Zelewsky, A.; Burger, P. Inorg. Chem. 2001, 40, 5675. For overviews on the synthesis and application of 2,2′-bipyridines, see: (h) Knof, U.; von Zelewsky, A. Angew. Chem., Int. Ed. 1999, 38, 303. (i) Chelucci, G.; Thummel, R. P. Chem. Rev. 2002, 102, 3129.
24. (a) Hayoz, P.; von Zelewsky, A. Tetrahedron Lett. 1992, 33, 5165. (b) Fletcher, N. C.; Keene, F. R.; Ziegler, M.; Stoeckli-Evans, H.; Viebrock, H.; von Zelewsky, A. Helv. Chim. Acta 1996, 79, 1192. (c) Gianini, M.; von Zelewsky, A. Synthesis 1996, 702. (d) Mamula, O.; von Zelewsky, A.; Bark, T.; Bernardinelli, G. Angew. Chem., Int. Ed. 1999, 38, 2945. (e) Lötscher, D.; Rupprecht, S.; Stoeckli-Evans, H.; von Zelewsky, A. Tetrahedron: Asymmetry 2000, 11, 4341. (f) Kolp, B.; Abeln, D.; Stoeckli-Evans, H.; von Zelewsky, A. Eur. J. Inorg. Chem. 2001, 1207. (g) Lötscher, D.; Rupprecht, S.; Collomb, P.; Belser, P.; Viebrock, H.; von Zelewsky, A.; Burger, P. Inorg. Chem. 2001, 40, 5675. For overviews on the synthesis and application of 2,2′-bipyridines, see: (h) Knof, U.; von Zelewsky, A. Angew. Chem., Int. Ed. 1999, 38, 303. (i) Chelucci, G.; Thummel, R. P. Chem. Rev. 2002, 102, 3129.
25. (a) Hayoz, P.; von Zelewsky, A. Tetrahedron Lett. 1992, 33, 5165. (b) Fletcher, N. C.; Keene, F. R.; Ziegler, M.; Stoeckli-Evans, H.; Viebrock, H.; von Zelewsky, A. Helv. Chim. Acta 1996, 79, 1192. (c) Gianini, M.; von Zelewsky, A. Synthesis 1996, 702. (d) Mamula, O.; von Zelewsky, A.; Bark, T.; Bernardinelli, G. Angew. Chem., Int. Ed. 1999, 38, 2945. (e) Lötscher, D.; Rupprecht, S.; Stoeckli-Evans, H.; von Zelewsky, A. Tetrahedron: Asymmetry 2000, 11, 4341. (f) Kolp, B.; Abeln, D.; Stoeckli-Evans, H.; von Zelewsky, A. Eur. J. Inorg. Chem. 2001, 1207. (g) Lötscher, D.; Rupprecht, S.; Collomb, P.; Belser, P.; Viebrock, H.; von Zelewsky, A.; Burger, P. Inorg. Chem. 2001, 40, 5675. For overviews on the synthesis and application of 2,2′-bipyridines, see: (h) Knof, U.; von Zelewsky, A. Angew. Chem., Int. Ed. 1999, 38, 303. (i) Chelucci, G.; Thummel, R. P. Chem. Rev. 2002, 102, 3129.
26. (a) Hayoz, P.; von Zelewsky, A. Tetrahedron Lett. 1992, 33, 5165. (b) Fletcher, N. C.; Keene, F. R.; Ziegler, M.; Stoeckli-Evans, H.; Viebrock, H.; von Zelewsky, A. Helv. Chim. Acta 1996, 79, 1192. (c) Gianini, M.; von Zelewsky, A. Synthesis 1996, 702. (d) Mamula, O.; von Zelewsky, A.; Bark, T.; Bernardinelli, G. Angew. Chem., Int. Ed. 1999, 38, 2945. (e) Lötscher, D.; Rupprecht, S.; Stoeckli-Evans, H.; von Zelewsky, A. Tetrahedron: Asymmetry 2000, 11, 4341. (f) Kolp, B.; Abeln, D.; Stoeckli-Evans, H.; von Zelewsky, A. Eur. J. Inorg. Chem. 2001, 1207. (g) Lötscher, D.; Rupprecht, S.; Collomb, P.; Belser, P.; Viebrock, H.; von Zelewsky, A.; Burger, P. Inorg. Chem. 2001, 40, 5675. For overviews on the synthesis and application of 2,2′-bipyridines, see: (h) Knof, U.; von Zelewsky, A. Angew. Chem., Int. Ed. 1999, 38, 303. (i) Chelucci, G.; Thummel, R. P. Chem. Rev. 2002, 102, 3129.
27. (a) Hayoz, P.; von Zelewsky, A. Tetrahedron Lett. 1992, 33, 5165. (b) Fletcher, N. C.; Keene, F. R.; Ziegler, M.; Stoeckli-Evans, H.; Viebrock, H.; von Zelewsky, A. Helv. Chim. Acta 1996, 79, 1192. (c) Gianini, M.; von Zelewsky, A. Synthesis 1996, 702. (d) Mamula, O.; von Zelewsky, A.; Bark, T.; Bernardinelli, G. Angew. Chem., Int. Ed. 1999, 38, 2945. (e) Lötscher, D.; Rupprecht, S.; Stoeckli-Evans, H.; von Zelewsky, A. Tetrahedron: Asymmetry 2000, 11, 4341. (f) Kolp, B.; Abeln, D.; Stoeckli-Evans, H.; von Zelewsky, A. Eur. J. Inorg. Chem. 2001, 1207. (g) Lötscher, D.; Rupprecht, S.; Collomb, P.; Belser, P.; Viebrock, H.; von Zelewsky, A.; Burger, P. Inorg. Chem. 2001, 40, 5675. For overviews on the synthesis and application of 2,2′-bipyridines, see: (h) Knof, U.; von Zelewsky, A. Angew. Chem., Int. Ed. 1999, 38, 303. (i) Chelucci, G.; Thummel, R. P. Chem. Rev. 2002, 102, 3129.
28. For other chiral pyridine derivatives, see, for example: (a) Chelucci, G.; Pinna, G. A.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 2571. (b) Chelucci, G. Tetrahedron: Asymmetry 1997, 8, 2667. (c) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (d) Chelucci, G.; Berta, D.; Saba, A. Tetrahedron 1997, 53, 3843. (e) Chelucci, G.; Saba, A.; Soccolini, F. Tetrahedron 2001, 57, 9989. (f) Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem. 1997, 62, 1604. (g) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437. (h) Wärnmark, K.; Stranne, R.; Cernerud, M.; Terrien, I.; Rahm, F.; Nordström, K.; Moberg, C. Acta Chem. Scand. 1998, 52, 961. For a recent overview of chiral pyridines, see: (i) Moberg, C.; Adolfsson, H.; Wärnmark, K. Acta Chem. Scand. 1996, 50, 195. (j) Canal, J. M.; Gómez, M.; Jiménez, F; Rocamora, M.; Muller, G.; Duñach, E.; Franco, D.; Jiménez, A.; Cano, F. H. Organometallics 2000, 19, 966. For recent examples of bipyridine ligands with planar chirality, see: (k) Wörsdorför, U.; Vögtle, F.; Nieger, M.; Waletzke, M.; Grimme, S.; Glorius, F.; Pfaltz, A. Synthesis 1999, 597. (l) Rios, R.; Liang, J.; Mo, M. M.-C.; Fu, G. C. Chem. Commun. 2000, 377. (m) Djukic, J.-P.; Michon, C.; Maisse-Franqois, A.; Allagapen, R.; Pfeffer, M.; Dötz, K. H.; De Cian, A.; Fischer, J. Chem. Eur. J. 2000, 6, 1064. For recent examples of chiral terpyridines and their use in asymmetric cyclopropanation, see: (n) Kwong, H.-L.; Lee, W. S. Tetrahedron: Asymmetry 2000, 11, 2299. (o) Kwong, H.-L.; Wong, W. L.; Lee, W.-S.; Cheng, L. S.; Wong, W.-T. Tetrahedron: Asymmetry 2001, 12, 2683.
29. For other chiral pyridine derivatives, see, for example: (a) Chelucci, G.; Pinna, G. A.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 2571. (b) Chelucci, G. Tetrahedron: Asymmetry 1997, 8, 2667. (c) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (d) Chelucci, G.; Berta, D.; Saba, A. Tetrahedron 1997, 53, 3843. (e) Chelucci, G.; Saba, A.; Soccolini, F. Tetrahedron 2001, 57, 9989. (f) Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem. 1997, 62, 1604. (g) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437. (h) Wärnmark, K.; Stranne, R.; Cernerud, M.; Terrien, I.; Rahm, F.; Nordström, K.; Moberg, C. Acta Chem. Scand. 1998, 52, 961. For a recent overview of chiral pyridines, see: (i) Moberg, C.; Adolfsson, H.; Wärnmark, K. Acta Chem. Scand. 1996, 50, 195. (j) Canal, J. M.; Gómez, M.; Jiménez, F; Rocamora, M.; Muller, G.; Duñach, E.; Franco, D.; Jiménez, A.; Cano, F. H. Organometallics 2000, 19, 966. For recent examples of bipyridine ligands with planar chirality, see: (k) Wörsdorför, U.; Vögtle, F.; Nieger, M.; Waletzke, M.; Grimme, S.; Glorius, F.; Pfaltz, A. Synthesis 1999, 597. (l) Rios, R.; Liang, J.; Mo, M. M.-C.; Fu, G. C. Chem. Commun. 2000, 377. (m) Djukic, J.-P.; Michon, C.; Maisse-Franqois, A.; Allagapen, R.; Pfeffer, M.; Dötz, K. H.; De Cian, A.; Fischer, J. Chem. Eur. J. 2000, 6, 1064. For recent examples of chiral terpyridines and their use in asymmetric cyclopropanation, see: (n) Kwong, H.-L.; Lee, W. S. Tetrahedron: Asymmetry 2000, 11, 2299. (o) Kwong, H.-L.; Wong, W. L.; Lee, W.-S.; Cheng, L. S.; Wong, W.-T. Tetrahedron: Asymmetry 2001, 12, 2683.
30. For other chiral pyridine derivatives, see, for example: (a) Chelucci, G.; Pinna, G. A.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 2571. (b) Chelucci, G. Tetrahedron: Asymmetry 1997, 8, 2667. (c) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (d) Chelucci, G.; Berta, D.; Saba, A. Tetrahedron 1997, 53, 3843. (e) Chelucci, G.; Saba, A.; Soccolini, F. Tetrahedron 2001, 57, 9989. (f) Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem. 1997, 62, 1604. (g) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437. (h) Wärnmark, K.; Stranne, R.; Cernerud, M.; Terrien, I.; Rahm, F.; Nordström, K.; Moberg, C. Acta Chem. Scand. 1998, 52, 961. For a recent overview of chiral pyridines, see: (i) Moberg, C.; Adolfsson, H.; Wärnmark, K. Acta Chem. Scand. 1996, 50, 195. (j) Canal, J. M.; Gómez, M.; Jiménez, F; Rocamora, M.; Muller, G.; Duñach, E.; Franco, D.; Jiménez, A.; Cano, F. H. Organometallics 2000, 19, 966. For recent examples of bipyridine ligands with planar chirality, see: (k) Wörsdorför, U.; Vögtle, F.; Nieger, M.; Waletzke, M.; Grimme, S.; Glorius, F.; Pfaltz, A. Synthesis 1999, 597. (l) Rios, R.; Liang, J.; Mo, M. M.-C.; Fu, G. C. Chem. Commun. 2000, 377. (m) Djukic, J.-P.; Michon, C.; Maisse-Franqois, A.; Allagapen, R.; Pfeffer, M.; Dötz, K. H.; De Cian, A.; Fischer, J. Chem. Eur. J. 2000, 6, 1064. For recent examples of chiral terpyridines and their use in asymmetric cyclopropanation, see: (n) Kwong, H.-L.; Lee, W. S. Tetrahedron: Asymmetry 2000, 11, 2299. (o) Kwong, H.-L.; Wong, W. L.; Lee, W.-S.; Cheng, L. S.; Wong, W.-T. Tetrahedron: Asymmetry 2001, 12, 2683.
31. For other chiral pyridine derivatives, see, for example: (a) Chelucci, G.; Pinna, G. A.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 2571. (b) Chelucci, G. Tetrahedron: Asymmetry 1997, 8, 2667. (c) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (d) Chelucci, G.; Berta, D.; Saba, A. Tetrahedron 1997, 53, 3843. (e) Chelucci, G.; Saba, A.; Soccolini, F. Tetrahedron 2001, 57, 9989. (f) Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem. 1997, 62, 1604. (g) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437. (h) Wärnmark, K.; Stranne, R.; Cernerud, M.; Terrien, I.; Rahm, F.; Nordström, K.; Moberg, C. Acta Chem. Scand. 1998, 52, 961. For a recent overview of chiral pyridines, see: (i) Moberg, C.; Adolfsson, H.; Wärnmark, K. Acta Chem. Scand. 1996, 50, 195. (j) Canal, J. M.; Gómez, M.; Jiménez, F; Rocamora, M.; Muller, G.; Duñach, E.; Franco, D.; Jiménez, A.; Cano, F. H. Organometallics 2000, 19, 966. For recent examples of bipyridine ligands with planar chirality, see: (k) Wörsdorför, U.; Vögtle, F.; Nieger, M.; Waletzke, M.; Grimme, S.; Glorius, F.; Pfaltz, A. Synthesis 1999, 597. (l) Rios, R.; Liang, J.; Mo, M. M.-C.; Fu, G. C. Chem. Commun. 2000, 377. (m) Djukic, J.-P.; Michon, C.; Maisse-Franqois, A.; Allagapen, R.; Pfeffer, M.; Dötz, K. H.; De Cian, A.; Fischer, J. Chem. Eur. J. 2000, 6, 1064. For recent examples of chiral terpyridines and their use in asymmetric cyclopropanation, see: (n) Kwong, H.-L.; Lee, W. S. Tetrahedron: Asymmetry 2000, 11, 2299. (o) Kwong, H.-L.; Wong, W. L.; Lee, W.-S.; Cheng, L. S.; Wong, W.-T. Tetrahedron: Asymmetry 2001, 12, 2683.
32. For other chiral pyridine derivatives, see, for example: (a) Chelucci, G.; Pinna, G. A.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 2571. (b) Chelucci, G. Tetrahedron: Asymmetry 1997, 8, 2667. (c) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (d) Chelucci, G.; Berta, D.; Saba, A. Tetrahedron 1997, 53, 3843. (e) Chelucci, G.; Saba, A.; Soccolini, F. Tetrahedron 2001, 57, 9989. (f) Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem. 1997, 62, 1604. (g) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437. (h) Wärnmark, K.; Stranne, R.; Cernerud, M.; Terrien, I.; Rahm, F.; Nordström, K.; Moberg, C. Acta Chem. Scand. 1998, 52, 961. For a recent overview of chiral pyridines, see: (i) Moberg, C.; Adolfsson, H.; Wärnmark, K. Acta Chem. Scand. 1996, 50, 195. (j) Canal, J. M.; Gómez, M.; Jiménez, F; Rocamora, M.; Muller, G.; Duñach, E.; Franco, D.; Jiménez, A.; Cano, F. H. Organometallics 2000, 19, 966. For recent examples of bipyridine ligands with planar chirality, see: (k) Wörsdorför, U.; Vögtle, F.; Nieger, M.; Waletzke, M.; Grimme, S.; Glorius, F.; Pfaltz, A. Synthesis 1999, 597. (l) Rios, R.; Liang, J.; Mo, M. M.-C.; Fu, G. C. Chem. Commun. 2000, 377. (m) Djukic, J.-P.; Michon, C.; Maisse-Franqois, A.; Allagapen, R.; Pfeffer, M.; Dötz, K. H.; De Cian, A.; Fischer, J. Chem. Eur. J. 2000, 6, 1064. For recent examples of chiral terpyridines and their use in asymmetric cyclopropanation, see: (n) Kwong, H.-L.; Lee, W. S. Tetrahedron: Asymmetry 2000, 11, 2299. (o) Kwong, H.-L.; Wong, W. L.; Lee, W.-S.; Cheng, L. S.; Wong, W.-T. Tetrahedron: Asymmetry 2001, 12, 2683.
33. For other chiral pyridine derivatives, see, for example: (a) Chelucci, G.; Pinna, G. A.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 2571. (b) Chelucci, G. Tetrahedron: Asymmetry 1997, 8, 2667. (c) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (d) Chelucci, G.; Berta, D.; Saba, A. Tetrahedron 1997, 53, 3843. (e) Chelucci, G.; Saba, A.; Soccolini, F. Tetrahedron 2001, 57, 9989. (f) Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem. 1997, 62, 1604. (g) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437. (h) Wärnmark, K.; Stranne, R.; Cernerud, M.; Terrien, I.; Rahm, F.; Nordström, K.; Moberg, C. Acta Chem. Scand. 1998, 52, 961. For a recent overview of chiral pyridines, see: (i) Moberg, C.; Adolfsson, H.; Wärnmark, K. Acta Chem. Scand. 1996, 50, 195. (j) Canal, J. M.; Gómez, M.; Jiménez, F; Rocamora, M.; Muller, G.; Duñach, E.; Franco, D.; Jiménez, A.; Cano, F. H. Organometallics 2000, 19, 966. For recent examples of bipyridine ligands with planar chirality, see: (k) Wörsdorför, U.; Vögtle, F.; Nieger, M.; Waletzke, M.; Grimme, S.; Glorius, F.; Pfaltz, A. Synthesis 1999, 597. (l) Rios, R.; Liang, J.; Mo, M. M.-C.; Fu, G. C. Chem. Commun. 2000, 377. (m) Djukic, J.-P.; Michon, C.; Maisse-Franqois, A.; Allagapen, R.; Pfeffer, M.; Dötz, K. H.; De Cian, A.; Fischer, J. Chem. Eur. J. 2000, 6, 1064. For recent examples of chiral terpyridines and their use in asymmetric cyclopropanation, see: (n) Kwong, H.-L.; Lee, W. S. Tetrahedron: Asymmetry 2000, 11, 2299. (o) Kwong, H.-L.; Wong, W. L.; Lee, W.-S.; Cheng, L. S.; Wong, W.-T. Tetrahedron: Asymmetry 2001, 12, 2683.
34. For other chiral pyridine derivatives, see, for example: (a) Chelucci, G.; Pinna, G. A.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 2571. (b) Chelucci, G. Tetrahedron: Asymmetry 1997, 8, 2667. (c) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (d) Chelucci, G.; Berta, D.; Saba, A. Tetrahedron 1997, 53, 3843. (e) Chelucci, G.; Saba, A.; Soccolini, F. Tetrahedron 2001, 57, 9989. (f) Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem. 1997, 62, 1604. (g) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437. (h) Wärnmark, K.; Stranne, R.; Cernerud, M.; Terrien, I.; Rahm, F.; Nordström, K.; Moberg, C. Acta Chem. Scand. 1998, 52, 961. For a recent overview of chiral pyridines, see: (i) Moberg, C.; Adolfsson, H.; Wärnmark, K. Acta Chem. Scand. 1996, 50, 195. (j) Canal, J. M.; Gómez, M.; Jiménez, F; Rocamora, M.; Muller, G.; Duñach, E.; Franco, D.; Jiménez, A.; Cano, F. H. Organometallics 2000, 19, 966. For recent examples of bipyridine ligands with planar chirality, see: (k) Wörsdorför, U.; Vögtle, F.; Nieger, M.; Waletzke, M.; Grimme, S.; Glorius, F.; Pfaltz, A. Synthesis 1999, 597. (l) Rios, R.; Liang, J.; Mo, M. M.-C.; Fu, G. C. Chem. Commun. 2000, 377. (m) Djukic, J.-P.; Michon, C.; Maisse-Franqois, A.; Allagapen, R.; Pfeffer, M.; Dötz, K. H.; De Cian, A.; Fischer, J. Chem. Eur. J. 2000, 6, 1064. For recent examples of chiral terpyridines and their use in asymmetric cyclopropanation, see: (n) Kwong, H.-L.; Lee, W. S. Tetrahedron: Asymmetry 2000, 11, 2299. (o) Kwong, H.-L.; Wong, W. L.; Lee, W.-S.; Cheng, L. S.; Wong, W.-T. Tetrahedron: Asymmetry 2001, 12, 2683.
35. For other chiral pyridine derivatives, see, for example: (a) Chelucci, G.; Pinna, G. A.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 2571. (b) Chelucci, G. Tetrahedron: Asymmetry 1997, 8, 2667. (c) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (d) Chelucci, G.; Berta, D.; Saba, A. Tetrahedron 1997, 53, 3843. (e) Chelucci, G.; Saba, A.; Soccolini, F. Tetrahedron 2001, 57, 9989. (f) Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem. 1997, 62, 1604. (g) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437. (h) Wärnmark, K.; Stranne, R.; Cernerud, M.; Terrien, I.; Rahm, F.; Nordström, K.; Moberg, C. Acta Chem. Scand. 1998, 52, 961. For a recent overview of chiral pyridines, see: (i) Moberg, C.; Adolfsson, H.; Wärnmark, K. Acta Chem. Scand. 1996, 50, 195. (j) Canal, J. M.; Gómez, M.; Jiménez, F; Rocamora, M.; Muller, G.; Duñach, E.; Franco, D.; Jiménez, A.; Cano, F. H. Organometallics 2000, 19, 966. For recent examples of bipyridine ligands with planar chirality, see: (k) Wörsdorför, U.; Vögtle, F.; Nieger, M.; Waletzke, M.; Grimme, S.; Glorius, F.; Pfaltz, A. Synthesis 1999, 597. (l) Rios, R.; Liang, J.; Mo, M. M.-C.; Fu, G. C. Chem. Commun. 2000, 377. (m) Djukic, J.-P.; Michon, C.; Maisse-Franqois, A.; Allagapen, R.; Pfeffer, M.; Dötz, K. H.; De Cian, A.; Fischer, J. Chem. Eur. J. 2000, 6, 1064. For recent examples of chiral terpyridines and their use in asymmetric cyclopropanation, see: (n) Kwong, H.-L.; Lee, W. S. Tetrahedron: Asymmetry 2000, 11, 2299. (o) Kwong, H.-L.; Wong, W. L.; Lee, W.-S.; Cheng, L. S.; Wong, W.-T. Tetrahedron: Asymmetry 2001, 12, 2683.
36. For other chiral pyridine derivatives, see, for example: (a) Chelucci, G.; Pinna, G. A.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 2571. (b) Chelucci, G. Tetrahedron: Asymmetry 1997, 8, 2667. (c) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (d) Chelucci, G.; Berta, D.; Saba, A. Tetrahedron 1997, 53, 3843. (e) Chelucci, G.; Saba, A.; Soccolini, F. Tetrahedron 2001, 57, 9989. (f) Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem. 1997, 62, 1604. (g) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437. (h) Wärnmark, K.; Stranne, R.; Cernerud, M.; Terrien, I.; Rahm, F.; Nordström, K.; Moberg, C. Acta Chem. Scand. 1998, 52, 961. For a recent overview of chiral pyridines, see: (i) Moberg, C.; Adolfsson, H.; Wärnmark, K. Acta Chem. Scand. 1996, 50, 195. (j) Canal, J. M.; Gómez, M.; Jiménez, F; Rocamora, M.; Muller, G.; Duñach, E.; Franco, D.; Jiménez, A.; Cano, F. H. Organometallics 2000, 19, 966. For recent examples of bipyridine ligands with planar chirality, see: (k) Wörsdorför, U.; Vögtle, F.; Nieger, M.; Waletzke, M.; Grimme, S.; Glorius, F.; Pfaltz, A. Synthesis 1999, 597. (l) Rios, R.; Liang, J.; Mo, M. M.-C.; Fu, G. C. Chem. Commun. 2000, 377. (m) Djukic, J.-P.; Michon, C.; Maisse-Franqois, A.; Allagapen, R.; Pfeffer, M.; Dötz, K. H.; De Cian, A.; Fischer, J. Chem. Eur. J. 2000, 6, 1064. For recent examples of chiral terpyridines and their use in asymmetric cyclopropanation, see: (n) Kwong, H.-L.; Lee, W. S. Tetrahedron: Asymmetry 2000, 11, 2299. (o) Kwong, H.-L.; Wong, W. L.; Lee, W.-S.; Cheng, L. S.; Wong, W.-T. Tetrahedron: Asymmetry 2001, 12, 2683.
37. For other chiral pyridine derivatives, see, for example: (a) Chelucci, G.; Pinna, G. A.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 2571. (b) Chelucci, G. Tetrahedron: Asymmetry 1997, 8, 2667. (c) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (d) Chelucci, G.; Berta, D.; Saba, A. Tetrahedron 1997, 53, 3843. (e) Chelucci, G.; Saba, A.; Soccolini, F. Tetrahedron 2001, 57, 9989. (f) Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem. 1997, 62, 1604. (g) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437. (h) Wärnmark, K.; Stranne, R.; Cernerud, M.; Terrien, I.; Rahm, F.; Nordström, K.; Moberg, C. Acta Chem. Scand. 1998, 52, 961. For a recent overview of chiral pyridines, see: (i) Moberg, C.; Adolfsson, H.; Wärnmark, K. Acta Chem. Scand. 1996, 50, 195. (j) Canal, J. M.; Gómez, M.; Jiménez, F; Rocamora, M.; Muller, G.; Duñach, E.; Franco, D.; Jiménez, A.; Cano, F. H. Organometallics 2000, 19, 966. For recent examples of bipyridine ligands with planar chirality, see: (k) Wörsdorför, U.; Vögtle, F.; Nieger, M.; Waletzke, M.; Grimme, S.; Glorius, F.; Pfaltz, A. Synthesis 1999, 597. (l) Rios, R.; Liang, J.; Mo, M. M.-C.; Fu, G. C. Chem. Commun. 2000, 377. (m) Djukic, J.-P.; Michon, C.; Maisse-Franqois, A.; Allagapen, R.; Pfeffer, M.; Dötz, K. H.; De Cian, A.; Fischer, J. Chem. Eur. J. 2000, 6, 1064. For recent examples of chiral terpyridines and their use in asymmetric cyclopropanation, see: (n) Kwong, H.-L.; Lee, W. S. Tetrahedron: Asymmetry 2000, 11, 2299. (o) Kwong, H.-L.; Wong, W. L.; Lee, W.-S.; Cheng, L. S.; Wong, W.-T. Tetrahedron: Asymmetry 2001, 12, 2683.
38. For other chiral pyridine derivatives, see, for example: (a) Chelucci, G.; Pinna, G. A.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 2571. (b) Chelucci, G. Tetrahedron: Asymmetry 1997, 8, 2667. (c) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (d) Chelucci, G.; Berta, D.; Saba, A. Tetrahedron 1997, 53, 3843. (e) Chelucci, G.; Saba, A.; Soccolini, F. Tetrahedron 2001, 57, 9989. (f) Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem. 1997, 62, 1604. (g) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437. (h) Wärnmark, K.; Stranne, R.; Cernerud, M.; Terrien, I.; Rahm, F.; Nordström, K.; Moberg, C. Acta Chem. Scand. 1998, 52, 961. For a recent overview of chiral pyridines, see: (i) Moberg, C.; Adolfsson, H.; Wärnmark, K. Acta Chem. Scand. 1996, 50, 195. (j) Canal, J. M.; Gómez, M.; Jiménez, F; Rocamora, M.; Muller, G.; Duñach, E.; Franco, D.; Jiménez, A.; Cano, F. H. Organometallics 2000, 19, 966. For recent examples of bipyridine ligands with planar chirality, see: (k) Wörsdorför, U.; Vögtle, F.; Nieger, M.; Waletzke, M.; Grimme, S.; Glorius, F.; Pfaltz, A. Synthesis 1999, 597. (l) Rios, R.; Liang, J.; Mo, M. M.-C.; Fu, G. C. Chem. Commun. 2000, 377. (m) Djukic, J.-P.; Michon, C.; Maisse-Franqois, A.; Allagapen, R.; Pfeffer, M.; Dötz, K. H.; De Cian, A.; Fischer, J. Chem. Eur. J. 2000, 6, 1064. For recent examples of chiral terpyridines and their use in asymmetric cyclopropanation, see: (n) Kwong, H.-L.; Lee, W. S. Tetrahedron: Asymmetry 2000, 11, 2299. (o) Kwong, H.-L.; Wong, W. L.; Lee, W.-S.; Cheng, L. S.; Wong, W.-T. Tetrahedron: Asymmetry 2001, 12, 2683.
39. For other chiral pyridine derivatives, see, for example: (a) Chelucci, G.; Pinna, G. A.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 2571. (b) Chelucci, G. Tetrahedron: Asymmetry 1997, 8, 2667. (c) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (d) Chelucci, G.; Berta, D.; Saba, A. Tetrahedron 1997, 53, 3843. (e) Chelucci, G.; Saba, A.; Soccolini, F. Tetrahedron 2001, 57, 9989. (f) Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem. 1997, 62, 1604. (g) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437. (h) Wärnmark, K.; Stranne, R.; Cernerud, M.; Terrien, I.; Rahm, F.; Nordström, K.; Moberg, C. Acta Chem. Scand. 1998, 52, 961. For a recent overview of chiral pyridines, see: (i) Moberg, C.; Adolfsson, H.; Wärnmark, K. Acta Chem. Scand. 1996, 50, 195. (j) Canal, J. M.; Gómez, M.; Jiménez, F; Rocamora, M.; Muller, G.; Duñach, E.; Franco, D.; Jiménez, A.; Cano, F. H. Organometallics 2000, 19, 966. For recent examples of bipyridine ligands with planar chirality, see: (k) Wörsdorför, U.; Vögtle, F.; Nieger, M.; Waletzke, M.; Grimme, S.; Glorius, F.; Pfaltz, A. Synthesis 1999, 597. (l) Rios, R.; Liang, J.; Mo, M. M.-C.; Fu, G. C. Chem. Commun. 2000, 377. (m) Djukic, J.-P.; Michon, C.; Maisse-Franqois, A.; Allagapen, R.; Pfeffer, M.; Dötz, K. H.; De Cian, A.; Fischer, J. Chem. Eur. J. 2000, 6, 1064. For recent examples of chiral terpyridines and their use in asymmetric cyclopropanation, see: (n) Kwong, H.-L.; Lee, W. S. Tetrahedron: Asymmetry 2000, 11, 2299. (o) Kwong, H.-L.; Wong, W. L.; Lee, W.-S.; Cheng, L. S.; Wong, W.-T. Tetrahedron: Asymmetry 2001, 12, 2683.
40. For other chiral pyridine derivatives, see, for example: (a) Chelucci, G.; Pinna, G. A.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 2571. (b) Chelucci, G. Tetrahedron: Asymmetry 1997, 8, 2667. (c) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (d) Chelucci, G.; Berta, D.; Saba, A. Tetrahedron 1997, 53, 3843. (e) Chelucci, G.; Saba, A.; Soccolini, F. Tetrahedron 2001, 57, 9989. (f) Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem. 1997, 62, 1604. (g) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437. (h) Wärnmark, K.; Stranne, R.; Cernerud, M.; Terrien, I.; Rahm, F.; Nordström, K.; Moberg, C. Acta Chem. Scand. 1998, 52, 961. For a recent overview of chiral pyridines, see: (i) Moberg, C.; Adolfsson, H.; Wärnmark, K. Acta Chem. Scand. 1996, 50, 195. (j) Canal, J. M.; Gómez, M.; Jiménez, F; Rocamora, M.; Muller, G.; Duñach, E.; Franco, D.; Jiménez, A.; Cano, F. H. Organometallics 2000, 19, 966. For recent examples of bipyridine ligands with planar chirality, see: (k) Wörsdorför, U.; Vögtle, F.; Nieger, M.; Waletzke, M.; Grimme, S.; Glorius, F.; Pfaltz, A. Synthesis 1999, 597. (l) Rios, R.; Liang, J.; Mo, M. M.-C.; Fu, G. C. Chem. Commun. 2000, 377. (m) Djukic, J.-P.; Michon, C.; Maisse-Franqois, A.; Allagapen, R.; Pfeffer, M.; Dötz, K. H.; De Cian, A.; Fischer, J. Chem. Eur. J. 2000, 6, 1064. For recent examples of chiral terpyridines and their use in asymmetric cyclopropanation, see: (n) Kwong, H.-L.; Lee, W. S. Tetrahedron: Asymmetry 2000, 11, 2299. (o) Kwong, H.-L.; Wong, W. L.; Lee, W.-S.; Cheng, L. S.; Wong, W.-T. Tetrahedron: Asymmetry 2001, 12, 2683.
41. For other chiral pyridine derivatives, see, for example: (a) Chelucci, G.; Pinna, G. A.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 2571. (b) Chelucci, G. Tetrahedron: Asymmetry 1997, 8, 2667. (c) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (d) Chelucci, G.; Berta, D.; Saba, A. Tetrahedron 1997, 53, 3843. (e) Chelucci, G.; Saba, A.; Soccolini, F. Tetrahedron 2001, 57, 9989. (f) Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem. 1997, 62, 1604. (g) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437. (h) Wärnmark, K.; Stranne, R.; Cernerud, M.; Terrien, I.; Rahm, F.; Nordström, K.; Moberg, C. Acta Chem. Scand. 1998, 52, 961. For a recent overview of chiral pyridines, see: (i) Moberg, C.; Adolfsson, H.; Wärnmark, K. Acta Chem. Scand. 1996, 50, 195. (j) Canal, J. M.; Gómez, M.; Jiménez, F; Rocamora, M.; Muller, G.; Duñach, E.; Franco, D.; Jiménez, A.; Cano, F. H. Organometallics 2000, 19, 966. For recent examples of bipyridine ligands with planar chirality, see: (k) Wörsdorför, U.; Vögtle, F.; Nieger, M.; Waletzke, M.; Grimme, S.; Glorius, F.; Pfaltz, A. Synthesis 1999, 597. (l) Rios, R.; Liang, J.; Mo, M. M.-C.; Fu, G. C. Chem. Commun. 2000, 377. (m) Djukic, J.-P.; Michon, C.; Maisse-Franqois, A.; Allagapen, R.; Pfeffer, M.; Dötz, K. H.; De Cian, A.; Fischer, J. Chem. Eur. J. 2000, 6, 1064. For recent examples of chiral terpyridines and their use in asymmetric cyclopropanation, see: (n) Kwong, H.-L.; Lee, W. S. Tetrahedron: Asymmetry 2000, 11, 2299. (o) Kwong, H.-L.; Wong, W. L.; Lee, W.-S.; Cheng, L. S.; Wong, W.-T. Tetrahedron: Asymmetry 2001, 12, 2683.
42. For other chiral pyridine derivatives, see, for example: (a) Chelucci, G.; Pinna, G. A.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 2571. (b) Chelucci, G. Tetrahedron: Asymmetry 1997, 8, 2667. (c) Chelucci, G.; Medici, S.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 3183. (d) Chelucci, G.; Berta, D.; Saba, A. Tetrahedron 1997, 53, 3843. (e) Chelucci, G.; Saba, A.; Soccolini, F. Tetrahedron 2001, 57, 9989. (f) Nordström, K.; Macedo, E.; Moberg, C. J. Org. Chem. 1997, 62, 1604. (g) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437. (h) Wärnmark, K.; Stranne, R.; Cernerud, M.; Terrien, I.; Rahm, F.; Nordström, K.; Moberg, C. Acta Chem. Scand. 1998, 52, 961. For a recent overview of chiral pyridines, see: (i) Moberg, C.; Adolfsson, H.; Wärnmark, K. Acta Chem. Scand. 1996, 50, 195. (j) Canal, J. M.; Gómez, M.; Jiménez, F; Rocamora, M.; Muller, G.; Duñach, E.; Franco, D.; Jiménez, A.; Cano, F. H. Organometallics 2000, 19, 966. For recent examples of bipyridine ligands with planar chirality, see: (k) Wörsdorför, U.; Vögtle, F.; Nieger, M.; Waletzke, M.; Grimme, S.; Glorius, F.; Pfaltz, A. Synthesis 1999, 597. (l) Rios, R.; Liang, J.; Mo, M. M.-C.; Fu, G. C. Chem. Commun. 2000, 377. (m) Djukic, J.-P.; Michon, C.; Maisse-Franqois, A.; Allagapen, R.; Pfeffer, M.; Dötz, K. H.; De Cian, A.; Fischer, J. Chem. Eur. J. 2000, 6, 1064. For recent examples of chiral terpyridines and their use in asymmetric cyclopropanation, see: (n) Kwong, H.-L.; Lee, W. S. Tetrahedron: Asymmetry 2000, 11, 2299. (o) Kwong, H.-L.; Wong, W. L.; Lee, W.-S.; Cheng, L. S.; Wong, W.-T. Tetrahedron: Asymmetry 2001, 12, 2683.
43. For catalytic application of phenanthroline complexes: (a) Gladiali, S.; Chelucci, G.; Soccolini, F.; Delogu, G.; Chiessa, G. J. Organomet. Chem. 1989, 370, 285. (b) Peña-Cabrera, E.; Norrby, P.-O.; Sjögren, M.; Vitagliano, A.; De Felice, V.; Oslob, J.; Ishii, S.; O'Neill, D.; Åkermark, B.; Helquist, P. J. Am. Chem. Soc. 1996, 118, 4299. Related nonchiral phenanthrolines: (c) Oslob, J. D.; Åkermark, B.; Helquist, P.; Norrby, P.-O. Organometallics 1997, 16, 3015. (d) Hansson, S.; Norrby, P.-O.; Sjögren, M. P. T.; Åkermark, B. Organometallics 1993, 12, 4940. (e) Sjögren, M. P. T.; Hansson, S.; Åkermark, B. Organometallics 1994, 13, 1963. (f) Frisell, H.; Åkermark, B. Organometallics 1995, 14, 561. (g) Sjögren, M. P. T.; Frisell, H.; Åkermark, B. Organometallics 1997, 16, 942. (h) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Organometallics 1999, 18, 2884. (i) Chelucci, G.; Iuliano, A.; Muroni, D.; Saba, A. J. Mol. Catal. 2003, 191, 29. (j) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Synthesis 2003, 73.
44. For catalytic application of phenanthroline complexes: (a) Gladiali, S.; Chelucci, G.; Soccolini, F.; Delogu, G.; Chiessa, G. J. Organomet. Chem. 1989, 370, 285. (b) Peña-Cabrera, E.; Norrby, P.-O.; Sjögren, M.; Vitagliano, A.; De Felice, V.; Oslob, J.; Ishii, S.; O'Neill, D.; Åkermark, B.; Helquist, P. J. Am. Chem. Soc. 1996, 118, 4299. Related nonchiral phenanthrolines: (c) Oslob, J. D.; Åkermark, B.; Helquist, P.; Norrby, P.-O. Organometallics 1997, 16, 3015. (d) Hansson, S.; Norrby, P.-O.; Sjögren, M. P. T.; Åkermark, B. Organometallics 1993, 12, 4940. (e) Sjögren, M. P. T.; Hansson, S.; Åkermark, B. Organometallics 1994, 13, 1963. (f) Frisell, H.; Åkermark, B. Organometallics 1995, 14, 561. (g) Sjögren, M. P. T.; Frisell, H.; Åkermark, B. Organometallics 1997, 16, 942. (h) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Organometallics 1999, 18, 2884. (i) Chelucci, G.; Iuliano, A.; Muroni, D.; Saba, A. J. Mol. Catal. 2003, 191, 29. (j) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Synthesis 2003, 73.
45. For catalytic application of phenanthroline complexes: (a) Gladiali, S.; Chelucci, G.; Soccolini, F.; Delogu, G.; Chiessa, G. J. Organomet. Chem. 1989, 370, 285. (b) Peña-Cabrera, E.; Norrby, P.-O.; Sjögren, M.; Vitagliano, A.; De Felice, V.; Oslob, J.; Ishii, S.; O'Neill, D.; Åkermark, B.; Helquist, P. J. Am. Chem. Soc. 1996, 118, 4299. Related nonchiral phenanthrolines: (c) Oslob, J. D.; Åkermark, B.; Helquist, P.; Norrby, P.-O. Organometallics 1997, 16, 3015. (d) Hansson, S.; Norrby, P.-O.; Sjögren, M. P. T.; Åkermark, B. Organometallics 1993, 12, 4940. (e) Sjögren, M. P. T.; Hansson, S.; Åkermark, B. Organometallics 1994, 13, 1963. (f) Frisell, H.; Åkermark, B. Organometallics 1995, 14, 561. (g) Sjögren, M. P. T.; Frisell, H.; Åkermark, B. Organometallics 1997, 16, 942. (h) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Organometallics 1999, 18, 2884. (i) Chelucci, G.; Iuliano, A.; Muroni, D.; Saba, A. J. Mol. Catal. 2003, 191, 29. (j) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Synthesis 2003, 73.
46. For catalytic application of phenanthroline complexes: (a) Gladiali, S.; Chelucci, G.; Soccolini, F.; Delogu, G.; Chiessa, G. J. Organomet. Chem. 1989, 370, 285. (b) Peña-Cabrera, E.; Norrby, P.-O.; Sjögren, M.; Vitagliano, A.; De Felice, V.; Oslob, J.; Ishii, S.; O'Neill, D.; Åkermark, B.; Helquist, P. J. Am. Chem. Soc. 1996, 118, 4299. Related nonchiral phenanthrolines: (c) Oslob, J. D.; Åkermark, B.; Helquist, P.; Norrby, P.-O. Organometallics 1997, 16, 3015. (d) Hansson, S.; Norrby, P.-O.; Sjögren, M. P. T.; Åkermark, B. Organometallics 1993, 12, 4940. (e) Sjögren, M. P. T.; Hansson, S.; Åkermark, B. Organometallics 1994, 13, 1963. (f) Frisell, H.; Åkermark, B. Organometallics 1995, 14, 561. (g) Sjögren, M. P. T.; Frisell, H.; Åkermark, B. Organometallics 1997, 16, 942. (h) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Organometallics 1999, 18, 2884. (i) Chelucci, G.; Iuliano, A.; Muroni, D.; Saba, A. J. Mol. Catal. 2003, 191, 29. (j) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Synthesis 2003, 73.
47. For catalytic application of phenanthroline complexes: (a) Gladiali, S.; Chelucci, G.; Soccolini, F.; Delogu, G.; Chiessa, G. J. Organomet. Chem. 1989, 370, 285. (b) Peña-Cabrera, E.; Norrby, P.-O.; Sjögren, M.; Vitagliano, A.; De Felice, V.; Oslob, J.; Ishii, S.; O'Neill, D.; Åkermark, B.; Helquist, P. J. Am. Chem. Soc. 1996, 118, 4299. Related nonchiral phenanthrolines: (c) Oslob, J. D.; Åkermark, B.; Helquist, P.; Norrby, P.-O. Organometallics 1997, 16, 3015. (d) Hansson, S.; Norrby, P.-O.; Sjögren, M. P. T.; Åkermark, B. Organometallics 1993, 12, 4940. (e) Sjögren, M. P. T.; Hansson, S.; Åkermark, B. Organometallics 1994, 13, 1963. (f) Frisell, H.; Åkermark, B. Organometallics 1995, 14, 561. (g) Sjögren, M. P. T.; Frisell, H.; Åkermark, B. Organometallics 1997, 16, 942. (h) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Organometallics 1999, 18, 2884. (i) Chelucci, G.; Iuliano, A.; Muroni, D.; Saba, A. J. Mol. Catal. 2003, 191, 29. (j) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Synthesis 2003, 73.
48. For catalytic application of phenanthroline complexes: (a) Gladiali, S.; Chelucci, G.; Soccolini, F.; Delogu, G.; Chiessa, G. J. Organomet. Chem. 1989, 370, 285. (b) Peña-Cabrera, E.; Norrby, P.-O.; Sjögren, M.; Vitagliano, A.; De Felice, V.; Oslob, J.; Ishii, S.; O'Neill, D.; Åkermark, B.; Helquist, P. J. Am. Chem. Soc. 1996, 118, 4299. Related nonchiral phenanthrolines: (c) Oslob, J. D.; Åkermark, B.; Helquist, P.; Norrby, P.-O. Organometallics 1997, 16, 3015. (d) Hansson, S.; Norrby, P.-O.; Sjögren, M. P. T.; Åkermark, B. Organometallics 1993, 12, 4940. (e) Sjögren, M. P. T.; Hansson, S.; Åkermark, B. Organometallics 1994, 13, 1963. (f) Frisell, H.; Åkermark, B. Organometallics 1995, 14, 561. (g) Sjögren, M. P. T.; Frisell, H.; Åkermark, B. Organometallics 1997, 16, 942. (h) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Organometallics 1999, 18, 2884. (i) Chelucci, G.; Iuliano, A.; Muroni, D.; Saba, A. J. Mol. Catal. 2003, 191, 29. (j) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Synthesis 2003, 73.
49. For catalytic application of phenanthroline complexes: (a) Gladiali, S.; Chelucci, G.; Soccolini, F.; Delogu, G.; Chiessa, G. J. Organomet. Chem. 1989, 370, 285. (b) Peña-Cabrera, E.; Norrby, P.-O.; Sjögren, M.; Vitagliano, A.; De Felice, V.; Oslob, J.; Ishii, S.; O'Neill, D.; Åkermark, B.; Helquist, P. J. Am. Chem. Soc. 1996, 118, 4299. Related nonchiral phenanthrolines: (c) Oslob, J. D.; Åkermark, B.; Helquist, P.; Norrby, P.-O. Organometallics 1997, 16, 3015. (d) Hansson, S.; Norrby, P.-O.; Sjögren, M. P. T.; Åkermark, B. Organometallics 1993, 12, 4940. (e) Sjögren, M. P. T.; Hansson, S.; Åkermark, B. Organometallics 1994, 13, 1963. (f) Frisell, H.; Åkermark, B. Organometallics 1995, 14, 561. (g) Sjögren, M. P. T.; Frisell, H.; Åkermark, B. Organometallics 1997, 16, 942. (h) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Organometallics 1999, 18, 2884. (i) Chelucci, G.; Iuliano, A.; Muroni, D.; Saba, A. J. Mol. Catal. 2003, 191, 29. (j) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Synthesis 2003, 73.
50. For catalytic application of phenanthroline complexes: (a) Gladiali, S.; Chelucci, G.; Soccolini, F.; Delogu, G.; Chiessa, G. J. Organomet. Chem. 1989, 370, 285. (b) Peña-Cabrera, E.; Norrby, P.-O.; Sjögren, M.; Vitagliano, A.; De Felice, V.; Oslob, J.; Ishii, S.; O'Neill, D.; Åkermark, B.; Helquist, P. J. Am. Chem. Soc. 1996, 118, 4299. Related nonchiral phenanthrolines: (c) Oslob, J. D.; Åkermark, B.; Helquist, P.; Norrby, P.-O. Organometallics 1997, 16, 3015. (d) Hansson, S.; Norrby, P.-O.; Sjögren, M. P. T.; Åkermark, B. Organometallics 1993, 12, 4940. (e) Sjögren, M. P. T.; Hansson, S.; Åkermark, B. Organometallics 1994, 13, 1963. (f) Frisell, H.; Åkermark, B. Organometallics 1995, 14, 561. (g) Sjögren, M. P. T.; Frisell, H.; Åkermark, B. Organometallics 1997, 16, 942. (h) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Organometallics 1999, 18, 2884. (i) Chelucci, G.; Iuliano, A.; Muroni, D.; Saba, A. J. Mol. Catal. 2003, 191, 29. (j) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Synthesis 2003, 73.
51. For catalytic application of phenanthroline complexes: (a) Gladiali, S.; Chelucci, G.; Soccolini, F.; Delogu, G.; Chiessa, G. J. Organomet. Chem. 1989, 370, 285. (b) Peña-Cabrera, E.; Norrby, P.-O.; Sjögren, M.; Vitagliano, A.; De Felice, V.; Oslob, J.; Ishii, S.; O'Neill, D.; Åkermark, B.; Helquist, P. J. Am. Chem. Soc. 1996, 118, 4299. Related nonchiral phenanthrolines: (c) Oslob, J. D.; Åkermark, B.; Helquist, P.; Norrby, P.-O. Organometallics 1997, 16, 3015. (d) Hansson, S.; Norrby, P.-O.; Sjögren, M. P. T.; Åkermark, B. Organometallics 1993, 12, 4940. (e) Sjögren, M. P. T.; Hansson, S.; Åkermark, B. Organometallics 1994, 13, 1963. (f) Frisell, H.; Åkermark, B. Organometallics 1995, 14, 561. (g) Sjögren, M. P. T.; Frisell, H.; Åkermark, B. Organometallics 1997, 16, 942. (h) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Organometallics 1999, 18, 2884. (i) Chelucci, G.; Iuliano, A.; Muroni, D.; Saba, A. J. Mol. Catal. 2003, 191, 29. (j) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Synthesis 2003, 73.
52. For catalytic application of phenanthroline complexes: (a) Gladiali, S.; Chelucci, G.; Soccolini, F.; Delogu, G.; Chiessa, G. J. Organomet. Chem. 1989, 370, 285. (b) Peña-Cabrera, E.; Norrby, P.-O.; Sjögren, M.; Vitagliano, A.; De Felice, V.; Oslob, J.; Ishii, S.; O'Neill, D.; Åkermark, B.; Helquist, P. J. Am. Chem. Soc. 1996, 118, 4299. Related nonchiral phenanthrolines: (c) Oslob, J. D.; Åkermark, B.; Helquist, P.; Norrby, P.-O. Organometallics 1997, 16, 3015. (d) Hansson, S.; Norrby, P.-O.; Sjögren, M. P. T.; Åkermark, B. Organometallics 1993, 12, 4940. (e) Sjögren, M. P. T.; Hansson, S.; Åkermark, B. Organometallics 1994, 13, 1963. (f) Frisell, H.; Åkermark, B. Organometallics 1995, 14, 561. (g) Sjögren, M. P. T.; Frisell, H.; Åkermark, B. Organometallics 1997, 16, 942. (h) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Organometallics 1999, 18, 2884. (i) Chelucci, G.; Iuliano, A.; Muroni, D.; Saba, A. J. Mol. Catal. 2003, 191, 29. (j) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Synthesis 2003, 73.
53. 2 nitrogens and their ability to coordinate metals. For the first examples, see the following: (a) Glos, M.; Reiser, O. Org. Lett. 2000, 2, 2045. For a different strategy of tuning the electronics of the oxazoline ring, see: (b) Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Org. Chem. 2001, 66, 206. Further modifications of the nitrogen electronics can be expected from bis(imidazolines). For the first reports on the use of imidazoline-type ligands in asymmetric synthesis, see the following: (c) Dupont, J.; Ebeling, G.; Delgado, M. R.; Consorti, C. S.; Burrow, R.; Farrar, D. H.; Lough, A. J. Inorg. Chem. Commun. 2001, 4, 471. (d) Casey, M.; Smyth, M. P. Synlett 2003, 102.
54. 2 nitrogens and their ability to coordinate metals. For the first examples, see the following: (a) Glos, M.; Reiser, O. Org. Lett. 2000, 2, 2045. For a different strategy of tuning the electronics of the oxazoline ring, see: (b) Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Org. Chem. 2001, 66, 206. Further modifications of the nitrogen electronics can be expected from bis(imidazolines). For the first reports on the use of imidazoline-type ligands in asymmetric synthesis, see the following: (c) Dupont, J.; Ebeling, G.; Delgado, M. R.; Consorti, C. S.; Burrow, R.; Farrar, D. H.; Lough, A. J. Inorg. Chem. Commun. 2001, 4, 471. (d) Casey, M.; Smyth, M. P. Synlett 2003, 102.
55. 2 nitrogens and their ability to coordinate metals. For the first examples, see the following: (a) Glos, M.; Reiser, O. Org. Lett. 2000, 2, 2045. For a different strategy of tuning the electronics of the oxazoline ring, see: (b) Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Org. Chem. 2001, 66, 206. Further modifications of the nitrogen electronics can be expected from bis(imidazolines). For the first reports on the use of imidazoline-type ligands in asymmetric synthesis, see the following: (c) Dupont, J.; Ebeling, G.; Delgado, M. R.; Consorti, C. S.; Burrow, R.; Farrar, D. H.; Lough, A. J. Inorg. Chem. Commun. 2001, 4, 471. (d) Casey, M.; Smyth, M. P. Synlett 2003, 102.
56. 2 nitrogens and their ability to coordinate metals. For the first examples, see the following: (a) Glos, M.; Reiser, O. Org. Lett. 2000, 2, 2045. For a different strategy of tuning the electronics of the oxazoline ring, see: (b) Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Org. Chem. 2001, 66, 206. Further modifications of the nitrogen electronics can be expected from bis(imidazolines). For the first reports on the use of imidazoline-type ligands in asymmetric synthesis, see the following: (c) Dupont, J.; Ebeling, G.; Delgado, M. R.; Consorti, C. S.; Burrow, R.; Farrar, D. H.; Lough, A. J. Inorg. Chem. Commun. 2001, 4, 471. (d) Casey, M.; Smyth, M. P. Synlett 2003, 102.
57. For our recent efforts in the area of chiral 2,2′-bipyridines, see: (a) Malkov, A. V.; Bella, M.; Langer, V.; Kočovský, P. Org. Lett. 2000, 2, 3047. (b) Malkov, A. V.; Baxendale, I. R.; Fawcett, J.; Russell, D. R.; Langer, V.; Mansfield, D. J.; Valko, M.; Kočovský, P. Organometallics 2001, 20, 673. (c) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kočovský, P. Org. Lett. 2002, 4, 1047. For analogous (phosphinoaryl)pyridines, see: (d) Malkov, A. V.; Bella, M.; Stará, I. G.; Kočovský, P. Tetrahedron Lett. 2001, 42, 3045. For related, chiral monopyridines, see: (e) Malkov, A. V.; Bell, M.; Vassieu, M.; Bugatti, V.; Kočovský, P. J. Mol. Catal. A 2003, 196, 179. For an overview, see: (f) Malkov, A. V.; Kočovský, P. Curr. Org. Chem. 2003, in press.
58. For our recent efforts in the area of chiral 2,2′-bipyridines, see: (a) Malkov, A. V.; Bella, M.; Langer, V.; Kočovský, P. Org. Lett. 2000, 2, 3047. (b) Malkov, A. V.; Baxendale, I. R.; Fawcett, J.; Russell, D. R.; Langer, V.; Mansfield, D. J.; Valko, M.; Kočovský, P. Organometallics 2001, 20, 673. (c) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kočovský, P. Org. Lett. 2002, 4, 1047. For analogous (phosphinoaryl)pyridines, see: (d) Malkov, A. V.; Bella, M.; Stará, I. G.; Kočovský, P. Tetrahedron Lett. 2001, 42, 3045. For related, chiral monopyridines, see: (e) Malkov, A. V.; Bell, M.; Vassieu, M.; Bugatti, V.; Kočovský, P. J. Mol. Catal. A 2003, 196, 179. For an
59. For our recent efforts in the area of chiral 2,2′-bipyridines, see: (a) Malkov, A. V.; Bella, M.; Langer, V.; Kočovský, P. Org. Lett. 2000, 2, 3047. (b) Malkov, A. V.; Baxendale, I. R.; Fawcett, J.; Russell, D. R.; Langer, V.; Mansfield, D. J.; Valko, M.; Kočovský, P. Organometallics 2001, 20, 673. (c) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kočovský, P. Org. Lett. 2002, 4, 1047. For analogous (phosphinoaryl)pyridines, see: (d) Malkov, A. V.; Bella, M.; Stará, I. G.; Kočovský, P. Tetrahedron Lett. 2001, 42, 3045. For related, chiral monopyridines, see: (e) Malkov, A. V.; Bell, M.; Vassieu, M.; Bugatti, V.; Kočovský, P. J. Mol. Catal. A 2003, 196, 179. For an overview, see: (f) Malkov, A. V.; Kočovský, P. Curr. Org. Chem. 2003, in press.
60. For our recent efforts in the area of chiral 2,2′-bipyridines, see: (a) Malkov, A. V.; Bella, M.; Langer, V.; Kočovský, P. Org. Lett. 2000, 2, 3047. (b) Malkov, A. V.; Baxendale, I. R.; Fawcett, J.; Russell, D. R.; Langer, V.; Mansfield, D. J.; Valko, M.; Kočovský, P. Organometallics 2001, 20, 673. (c) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kočovský, P. Org. Lett. 2002, 4, 1047. For analogous (phosphinoaryl)pyridines, see: (d) Malkov, A. V.; Bella, M.; Stará, I. G.; Kočovský, P. Tetrahedron Lett. 2001, 42, 3045. For related, chiral monopyridines, see: (e) Malkov, A. V.; Bell, M.; Vassieu, M.; Bugatti, V.; Kočovský, P. J. Mol. Catal. A 2003, 196, 179. For an overview, see: (f) Malkov, A. V.; Kočovský, P. Curr. Org. Chem. 2003, in press.
61. For our recent efforts in the area of chiral 2,2′-bipyridines, see: (a) Malkov, A. V.; Bella, M.; Langer, V.; Kočovský, P. Org. Lett. 2000, 2, 3047. (b) Malkov, A. V.; Baxendale, I. R.; Fawcett, J.; Russell, D. R.; Langer, V.; Mansfield, D. J.; Valko, M.; Kočovský, P. Organometallics 2001, 20, 673. (c) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kočovský, P. Org. Lett. 2002, 4, 1047. For analogous (phosphinoaryl)pyridines, see: (d) Malkov, A. V.; Bella, M.; Stará, I. G.; Kočovský, P. Tetrahedron Lett. 2001, 42, 3045. For related, chiral monopyridines, see: (e) Malkov, A. V.; Bell, M.; Vassieu, M.; Bugatti, V.; Kočovský, P. J. Mol. Catal. A 2003, 196, 179. For an overview, see: (f) Malkov, A. V.; Kočovský, P. Curr. Org. Chem. 2003, in press.
62. For our recent efforts in the area of chiral 2,2′-bipyridines, see: (a) Malkov, A. V.; Bella, M.; Langer, V.; Kočovský, P. Org. Lett. 2000, 2, 3047. (b) Malkov, A. V.; Baxendale, I. R.; Fawcett, J.; Russell, D. R.; Langer, V.; Mansfield, D. J.; Valko, M.; Kočovský, P. Organometallics 2001, 20, 673. (c) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kočovský, P. Org. Lett. 2002, 4, 1047. For analogous (phosphinoaryl)pyridines, see: (d) Malkov, A. V.; Bella, M.; Stará, I. G.; Kočovský, P. Tetrahedron Lett. 2001, 42, 3045. For related, chiral monopyridines, see: (e) Malkov, A. V.; Bell, M.; Vassieu, M.; Bugatti, V.; Kočovský, P. J. Mol. Catal. A 2003, 196, 179. For an overview, see: (f) Malkov, A. V.; Kočovský, P. Curr. Org. Chem. 2003, in press.
63. 5e,f
64. For a conceptually different approach to 2,2′-bipyridines, based on the hetero-Diels-Alder reaction, see: (a) Bushby, N.; Moody, C. J.; Riddick, D. A.; Waldron, I. R. J. Chem. Soc., Perkin Trans. 1 2001, 2183. For a three-step double annulation, leading to analogous, axially chiral 2,2′-bipyridines, see: (b) Thumel, R. P.; Lefoulon, F. J. Org. Chem. 1985, 50, 666. (c) Nakajima, M.; Sasaku, Y.; Shiro, M. Tetrahedron: Asymmetry 1997, 8, 341. (d) Hashimoto, S.; Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419. (e) Nakajima, M.; Saito, M.; Hashimoto, S. Chem. Pharm. Bull. 2000, 48, 306.
65. For a conceptually different approach to 2,2′-bipyridines, based on the hetero-Diels-Alder reaction, see: (a) Bushby, N.; Moody, C. J.; Riddick, D. A.; Waldron, I. R. J. Chem. Soc., Perkin Trans. 1 2001, 2183. For a three-step double annulation, leading to analogous, axially chiral 2,2′-bipyridines, see: (b) Thumel, R. P.; Lefoulon, F. J. Org. Chem. 1985, 50, 666. (c) Nakajima, M.; Sasaku, Y.; Shiro, M. Tetrahedron: Asymmetry 1997, 8, 341. (d) Hashimoto, S.; Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419. (e) Nakajima, M.; Saito, M.; Hashimoto, S. Chem. Pharm. Bull. 2000, 48, 306.
66. For a conceptually different approach to 2,2′-bipyridines, based on the hetero-Diels-Alder reaction, see: (a) Bushby, N.; Moody, C. J.; Riddick, D. A.; Waldron, I. R. J. Chem. Soc., Perkin Trans. 1 2001, 2183. For a three-step double annulation, leading to analogous, axially chiral 2,2′-bipyridines, see: (b) Thumel, R. P.; Lefoulon, F. J. Org. Chem. 1985, 50, 666. (c) Nakajima, M.; Sasaku, Y.; Shiro, M. Tetrahedron: Asymmetry 1997, 8, 341. (d) Hashimoto, S.; Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419. (e) Nakajima, M.; Saito, M.; Hashimoto, S. Chem. Pharm. Bull. 2000, 48, 306.
67. For a conceptually different approach to 2,2′-bipyridines, based on the hetero-Diels-Alder reaction, see: (a) Bushby, N.; Moody, C. J.; Riddick, D. A.; Waldron, I. R. J. Chem. Soc., Perkin Trans. 1 2001, 2183. For a three-step double annulation, leading to analogous, axially chiral 2,2′-bipyridines, see: (b) Thumel, R. P.; Lefoulon, F. J. Org. Chem. 1985, 50, 666. (c) Nakajima, M.; Sasaku, Y.; Shiro, M. Tetrahedron: Asymmetry 1997, 8, 341. (d) Hashimoto, S.; Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419. (e) Nakajima, M.; Saito, M.; Hashimoto, S. Chem. Pharm. Bull. 2000, 48, 306.
68. For a conceptually different approach to 2,2′-bipyridines, based on the hetero-Diels-Alder reaction, see: (a) Bushby, N.; Moody, C. J.; Riddick, D. A.; Waldron, I. R. J. Chem. Soc., Perkin Trans. 1 2001, 2183. For a three-step double annulation, leading to analogous, axially chiral 2,2′-bipyridines, see: (b) Thumel, R. P.; Lefoulon, F. J. Org. Chem. 1985, 50, 666. (c) Nakajima, M.; Sasaku, Y.; Shiro, M. Tetrahedron: Asymmetry 1997, 8, 341. (d) Hashimoto, S.; Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419. (e) Nakajima, M.; Saito, M.; Hashimoto, S. Chem. Pharm. Bull. 2000, 48, 306.
69. 4g
70. Malkov, A. V.; Bella, M.; Langer, V.; Kočovský, P. Unpublished results.
71. 5g
72. 9d
73. Nopinone is commercially available but rather expensive.
74. (-)-β-Pinene (-)-10 was of 95% ee according to chiral GC. For determination of enantiopurity of monoterpene hydrocarbons by GC, see: Krüger, A.; Icheln, D.; Runge, T. J. High Resolut. Chromatogr. 1992, 15, 184.
75. Kozikowski, A. P.; Reddy, E. R.; Miller, C. P. J. Chem. Soc., Perkin Trans. 1 1990, 195-197.
76. For the method of an analogous dimerization of α-chloropyridines, see refs 5a, 9a,b, and the following: (a) Dehmlow, E. V.; Sleegers, A. Liebigs Ann. Chem. 1992, 9; 953. (b) Brenner, E.; Schneider, R.; Fort, Y. Tetrahedron Lett. 2000, 41, 2881.
77. For the method of an analogous dimerization of α-chloropyridines, see refs 5a, 9a,b, and the following: (a) Dehmlow, E. V.; Sleegers, A. Liebigs Ann. Chem. 1992, 9; 953. (b) Brenner, E.; Schneider, R.; Fort, Y. Tetrahedron Lett. 2000, 41, 2881.
78. (+)-3-Carene (+)-14 was of 93% ee (by GC).
79. (a) Rothenberg, G.; Yatziv, Y.; Sasson, Y. Tetrahedron 1998, 54, 593.
80. (b) Vyglazov, O. G.; Manukov, E. N.; Fedorishcheva, M. N.; Ariko, N. G.; Chuiko, V. A.; Bazhina, G. N. Chem. Nat. Compd. (Engl. Transl.) 1991, 27; Khim. Prir. Soedin. 1991, 328.
81. (b) Vyglazov, O. G.; Manukov, E. N.; Fedorishcheva, M. N.; Ariko, N. G.; Chuiko, V. A.; Bazhina, G. N. Chem. Nat. Compd. (Engl. Transl.) 1991, 27; Khim. Prir. Soedin. 1991, 328.
82. (a) Maas, D. D.; Blagg, M.; Wiemer, D. F. J. Org. Chem. 1984, 49, 853. For a less economical synthesis, see:
83. (b) Cocker, W.; Shannon, P. V. R.; Staniland, P. A. J. Chem. Soc. C 1967, 485.
84. For the Kröhnke annulation, see: (a) Kröhnke, F.; Heffe, W. Chem. Ber. 1937, 70, 864. For an overview, see: (b) Kröhnke, F. Synthesis 1976, 1. For a recent overview of its application in the synthesis of terpenoid bipyridines, see ref 5h,i.
85. For the Kröhnke annulation, see: (a) Kröhnke, F.; Heffe, W. Chem. Ber. 1937, 70, 864. For an overview, see: (b) Kröhnke, F. Synthesis 1976, 1. For a recent overview of its application in the synthesis of terpenoid bipyridines, see ref 5h,i.
86. The Kröhnke salt 19 was obtained on reaction of ethyl bromoacetate with pyridine; see ref 23. See also: (a) Kröhnke, F. Chem. Ber. 1940, 73, 310. (b) Neilands, O. Ya.; Shebenina, E. V.; Pukitis, G. G. Chem. Heterocycl. Compd. (Engl. Transl.) 1999, 35, 1443; Khim. Geterotsikl. Soedin. 1999, 1647. (c) Tsuge, O.; Kanemasa, S.; Takenaka, S. Bull. Chem. Soc. Jpn. 1985, 58, 3137. (d) Aldersley, M. F.; Dean, F. M.; Nayyir-Mazhir, R. J. Chem. Soc., Perkin Trans. 1 1983, 1753. Apparently, the Kröhnke salts derived from α-haloketones give much higher yields of the annulated products than those derived from α-haloesters.
87. The Kröhnke salt 19 was obtained on reaction of ethyl bromoacetate with pyridine; see ref 23. See also: (a) Kröhnke, F. Chem. Ber. 1940, 73, 310. (b) Neilands, O. Ya.; Shebenina, E. V.; Pukitis, G. G. Chem. Heterocycl. Compd. (Engl. Transl.) 1999, 35, 1443; Khim. Geterotsikl. Soedin. 1999, 1647. (c) Tsuge, O.; Kanemasa, S.; Takenaka, S. Bull. Chem. Soc. Jpn. 1985, 58, 3137. (d) Aldersley, M. F.; Dean, F. M.; Nayyir-Mazhir, R. J. Chem. Soc., Perkin Trans. 1 1983, 1753. Apparently, the Kröhnke salts derived from α-haloketones give much higher yields of the annulated products than those derived from α-haloesters.
88. The Kröhnke salt 19 was obtained on reaction of ethyl bromoacetate with pyridine; see ref 23. See also: (a) Kröhnke, F. Chem. Ber. 1940, 73, 310. (b) Neilands, O. Ya.; Shebenina, E. V.; Pukitis, G. G. Chem. Heterocycl. Compd. (Engl. Transl.) 1999, 35, 1443; Khim. Geterotsikl. Soedin. 1999, 1647. (c) Tsuge, O.; Kanemasa, S.; Takenaka, S. Bull. Chem. Soc. Jpn. 1985, 58, 3137. (d) Aldersley, M. F.; Dean, F. M.; Nayyir-Mazhir, R. J. Chem. Soc., Perkin Trans. 1 1983, 1753. Apparently, the Kröhnke salts derived from α-haloketones give much higher yields of the annulated products than those derived from α-haloesters.
89. The Kröhnke salt 19 was obtained on reaction of ethyl bromoacetate with pyridine; see ref 23. See also: (a) Kröhnke, F. Chem. Ber. 1940, 73, 310. (b) Neilands, O. Ya.; Shebenina, E. V.; Pukitis, G. G. Chem. Heterocycl. Compd. (Engl. Transl.) 1999, 35, 1443; Khim. Geterotsikl. Soedin. 1999, 1647. (c) Tsuge, O.; Kanemasa, S.; Takenaka, S. Bull. Chem. Soc. Jpn. 1985, 58, 3137. (d) Aldersley, M. F.; Dean, F. M.; Nayyir-Mazhir, R. J. Chem. Soc., Perkin Trans. 1 1983, 1753. Apparently, the Kröhnke salts derived from α-haloketones give much higher yields of the annulated products than those derived from α-haloesters.
90. The Kröhnke salt 19 was obtained on reaction of ethyl bromoacetate with pyridine; see ref 23. See also: (a) Kröhnke, F. Chem. Ber. 1940, 73, 310. (b) Neilands, O. Ya.; Shebenina, E. V.; Pukitis, G. G. Chem. Heterocycl. Compd. (Engl. Transl.) 1999, 35, 1443; Khim. Geterotsikl. Soedin. 1999, 1647. (c) Tsuge, O.; Kanemasa, S.; Takenaka, S. Bull. Chem. Soc. Jpn. 1985, 58, 3137. (d) Aldersley, M. F.; Dean, F. M.; Nayyir-Mazhir, R. J. Chem. Soc., Perkin Trans. 1 1983, 1753. Apparently, the Kröhnke salts derived from α-haloketones give much higher yields of the annulated products than those derived from α-haloesters.
91. Cocker, W.; Pratt, A. C.; Shannon, P. V. R. J. Chem. Soc. C 1968, 484.
92. For the method, see ref 9a,b and Burk, M. J.; Casy, G.; Johnson, N. B. J. Org. Chem. 1998, 63, 6084.
93. For the method, see ref 9a,b and Meth-Cohn, O.; Westwood, K. T. J. Chem. Soc., Perkin Trans. 1 1984, 1173.
94. Crombie, L.; Crombie, W.; Mary, L.; Jamieson, S. V.; Palmer, C. J. J. Chem. Soc., Perkin Trans. 1 1988, 1243.
95. A similar reaction with 3-carene epoxide has been reported to occur in 97% yield: Paquette, L. A.; Ross, R. J.; Shi, Y.-J. J. Org. Chem. 1990, 55, 1589.
96. Arbuzov, B. A.; Isaeva, Z. G.; Vil'chinskaya, A. R.; Belyaeva, M. G. Dokl. Chem. (Engl. Transl.) 1971, 199, 690; Dokl. Akad. Nauk SSSR Ser. Khim. 1971, 199, 1304.
97. Arbuzov, B. A.; Isaeva, Z. G.; Vil'chinskaya, A. R.; Belyaeva, M. G. Dokl. Chem. (Engl. Transl.) 1971, 199, 690; Dokl. Akad. Nauk SSSR Ser. Khim. 1971, 199, 1304.
98. Arbuzov, B. A.; Isaeva, Z. G.; Ratner, V. V. J. Org. Chem. USSR (Engl. Transl.) 1966, 2, 1391; Zh. Org. Khim. 1966, 2, 1401.
99. Arbuzov, B. A.; Isaeva, Z. G.; Ratner, V. V. J. Org. Chem. USSR (Engl. Transl.) 1966, 2, 1391; Zh. Org. Khim. 1966, 2, 1401.
100. See ref 22 and (a) Bellamy, A. J.; Crilly, W.; Farthing, J.; Kellie, G. M. J. Chem. Soc., Perkin Trans. 1 1974, 2417.
101. (b) Chidambaram, N.; Chandrasekaran, S. J. Org. Chem. 1987, 52, 5048.
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107. (a) Boyle, P. H.; Cocker, W.; Gordon, R. L.; Shannon, P. V. R. J. Chem. Soc. C 1971, 2127.
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109. Lochynski, S.; Walkowicz, M. Pol. J. Chem. 1982, 56, 1333.
110. It is crucial that the intramolecular aldol condensation is carried out with a <4% aqueous NaOH solution (see Experimental Section). Higher concentrations or using ethanol as the solvent leads to the deprotonation of the aldol product 36 in the allylic position, which triggers the opening of the cyclopropane ring to produce 1-acetyl-3,3-dimethyl-cyclohexa-1,4-diene. Therefore, the starting keto aldehyde 35 used in this reaction must be pure and alcohol-free.
111. 2 carbon, there was no need to separate the diastereoisomers.
112. Other oxidizing reagents are prone to open the cyclopropane ring.
113. This procedure clearly needs to be optimized in order to improve the yield; for a much higher yield in a related system, see Scheme 1.
114. 4, reflux, 24 h) produced pinocarvone in a mere 27% yield: Hartshorn, M. P.; Wallis, A. F. A. J. Chem. Soc. 1964, 5254.
115. The use of tert-butyl ester analogue of 19 led to a marginally higher yield.
116. 1H NMR spectrum of the bipyridine (+)-47 thus obtained showed no peaks corresponding to the minor meso-diastereoisomer.
117. 5f
118. (b) The alkylations are remarkably stereoselective (the alkylating reagent approaches from the less hindered face). The minor epimers formed (usually no more than 2%, as detected by NMR) were removed during the chromatographic purification.
119. (a) Ahmed, S.; Boruah, R. C. Tetrahedron Lett. 1996, 37, 8231.
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121. (a) Gokhale, A. S.; Minidis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831. (b) Andrus, M. A.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (c) Södergren, M. J.; Andersson,P. G. Tetrahedron Lett. 1996, 37, 7577. (d) Hamachi, K.; Irie, R.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4979. (e) Kawasaki, K.; Katsuki, T. Tetrahedron 1997, 53, 6337. (f) Clark, J. S.; Tolhurst, K. F.; Taylor, M.; Swallow, S. J. Chem. Soc., Perkin Trans. 1 1998, 1167. (g) Sekar, G.; DattaGupta, A.; Singh, V. K. J. Org. Chem. 1998, 63, 2961. (h) Kohmura, Y.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3941. (i) Andrus, M. B.; Asgari, D. Tetrahedron 2000, 56, 5775. (j) Lee, S.Z.; Kwong, H.-L.; Chan, H.-L.; Choi, W.-W.; Ng, L.-Y. Tetrahedron: Asymmetry 2001, 12, 1007. (k) Andrus, M. B.; Zhou, Z. J. Am. Chem. Soc. 2002, 124, 8806. (l) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Tetrahedron Lett. 2002, 43, 3601. (m) Chelucci, G.; Iuliano, A.; Muroni, D. Saba, A. J. Mol. Catal. A 2003, 191, 29. For mechanistic issues in the nonasymmetric, Ru-catalyzed allylic oxidation, see: (m) Stultz, R. T.; Huynh, M. H. V.; Binstead, R. A.; Curry, M.; Meyer, T. J. J. Am. Chem. Soc. 2000, 122, 5984. For reviews, see: (n) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567. (o) Andrus, M. B.; Lashley, J. Tetrahedron 2002, 58, 845.
122. (a) Gokhale, A. S.; Minidis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831. (b) Andrus, M. A.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (c) Södergren, M. J.; Andersson,P. G. Tetrahedron Lett. 1996, 37, 7577. (d) Hamachi, K.; Irie, R.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4979. (e) Kawasaki, K.; Katsuki, T. Tetrahedron 1997, 53, 6337. (f) Clark, J. S.; Tolhurst, K. F.; Taylor, M.; Swallow, S. J. Chem. Soc., Perkin Trans. 1 1998, 1167. (g) Sekar, G.; DattaGupta, A.; Singh, V. K. J. Org. Chem. 1998, 63, 2961. (h) Kohmura, Y.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3941. (i) Andrus, M. B.; Asgari, D. Tetrahedron 2000, 56, 5775. (j) Lee, S.Z.; Kwong, H.-L.; Chan, H.-L.; Choi, W.-W.; Ng, L.-Y. Tetrahedron: Asymmetry 2001, 12, 1007. (k) Andrus, M. B.; Zhou, Z. J. Am. Chem. Soc. 2002, 124, 8806. (l) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Tetrahedron Lett. 2002, 43, 3601. (m) Chelucci, G.; Iuliano, A.; Muroni, D. Saba, A. J. Mol. Catal. A 2003, 191, 29. For mechanistic issues in the nonasymmetric, Ru-catalyzed allylic oxidation, see: (m) Stultz, R. T.; Huynh, M. H. V.; Binstead, R. A.; Curry, M.; Meyer, T. J. J. Am. Chem. Soc. 2000, 122, 5984. For reviews, see: (n) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567. (o) Andrus, M. B.; Lashley, J. Tetrahedron 2002, 58, 845.
123. (a) Gokhale, A. S.; Minidis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831. (b) Andrus, M. A.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (c) Södergren, M. J.; Andersson,P. G. Tetrahedron Lett. 1996, 37, 7577. (d) Hamachi, K.; Irie, R.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4979. (e) Kawasaki, K.; Katsuki, T. Tetrahedron 1997, 53, 6337. (f) Clark, J. S.; Tolhurst, K. F.; Taylor, M.; Swallow, S. J. Chem. Soc., Perkin Trans. 1 1998, 1167. (g) Sekar, G.; DattaGupta, A.; Singh, V. K. J. Org. Chem. 1998, 63, 2961. (h) Kohmura, Y.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3941. (i) Andrus, M. B.; Asgari, D. Tetrahedron 2000, 56, 5775. (j) Lee, S.Z.; Kwong, H.-L.; Chan, H.-L.; Choi, W.-W.; Ng, L.-Y. Tetrahedron: Asymmetry 2001, 12, 1007. (k) Andrus, M. B.; Zhou, Z. J. Am. Chem. Soc. 2002, 124, 8806. (l) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Tetrahedron Lett. 2002, 43, 3601. (m) Chelucci, G.; Iuliano, A.; Muroni, D. Saba, A. J. Mol. Catal. A 2003, 191, 29. For mechanistic issues in the nonasymmetric, Ru-catalyzed allylic oxidation, see: (m) Stultz, R. T.; Huynh, M. H. V.; Binstead, R. A.; Curry, M.; Meyer, T. J. J. Am. Chem. Soc. 2000, 122, 5984. For reviews, see: (n) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567. (o) Andrus, M. B.; Lashley, J. Tetrahedron 2002, 58, 845.
124. (a) Gokhale, A. S.; Minidis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831. (b) Andrus, M. A.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (c) Södergren, M. J.; Andersson,P. G. Tetrahedron Lett. 1996, 37, 7577. (d) Hamachi, K.; Irie, R.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4979. (e) Kawasaki, K.; Katsuki, T. Tetrahedron 1997, 53, 6337. (f) Clark, J. S.; Tolhurst, K. F.; Taylor, M.; Swallow, S. J. Chem. Soc., Perkin Trans. 1 1998, 1167. (g) Sekar, G.; DattaGupta, A.; Singh, V. K. J. Org. Chem. 1998, 63, 2961. (h) Kohmura, Y.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3941. (i) Andrus, M. B.; Asgari, D. Tetrahedron 2000, 56, 5775. (j) Lee, S.Z.; Kwong, H.-L.; Chan, H.-L.; Choi, W.-W.; Ng, L.-Y. Tetrahedron: Asymmetry 2001, 12, 1007. (k) Andrus, M. B.; Zhou, Z. J. Am. Chem. Soc. 2002, 124, 8806. (l) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Tetrahedron Lett. 2002, 43, 3601. (m) Chelucci, G.; Iuliano, A.; Muroni, D. Saba, A. J. Mol. Catal. A 2003, 191, 29. For mechanistic issues in the nonasymmetric, Ru-catalyzed allylic oxidation, see: (m) Stultz, R. T.; Huynh, M. H. V.; Binstead, R. A.; Curry, M.; Meyer, T. J. J. Am. Chem. Soc. 2000, 122, 5984. For reviews, see: (n) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567. (o) Andrus, M. B.; Lashley, J. Tetrahedron 2002, 58, 845.
125. (a) Gokhale, A. S.; Minidis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831. (b) Andrus, M. A.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (c) Södergren, M. J.; Andersson,P. G. Tetrahedron Lett. 1996, 37, 7577. (d) Hamachi, K.; Irie, R.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4979. (e) Kawasaki, K.; Katsuki, T. Tetrahedron 1997, 53, 6337. (f) Clark, J. S.; Tolhurst, K. F.; Taylor, M.; Swallow, S. J. Chem. Soc., Perkin Trans. 1 1998, 1167. (g) Sekar, G.; DattaGupta, A.; Singh, V. K. J. Org. Chem. 1998, 63, 2961. (h) Kohmura, Y.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3941. (i) Andrus, M. B.; Asgari, D. Tetrahedron 2000, 56, 5775. (j) Lee, S.Z.; Kwong, H.-L.; Chan, H.-L.; Choi, W.-W.; Ng, L.-Y. Tetrahedron: Asymmetry 2001, 12, 1007. (k) Andrus, M. B.; Zhou, Z. J. Am. Chem. Soc. 2002, 124, 8806. (l) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Tetrahedron Lett. 2002, 43, 3601. (m) Chelucci, G.; Iuliano, A.; Muroni, D. Saba, A. J. Mol. Catal. A 2003, 191, 29. For mechanistic issues in the nonasymmetric, Ru-catalyzed allylic oxidation, see: (m) Stultz, R. T.; Huynh, M. H. V.; Binstead, R. A.; Curry, M.; Meyer, T. J. J. Am. Chem. Soc. 2000, 122, 5984. For reviews, see: (n) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567. (o) Andrus, M. B.; Lashley, J. Tetrahedron 2002, 58, 845.
126. (a) Gokhale, A. S.; Minidis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831. (b) Andrus, M. A.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (c) Södergren, M. J.; Andersson,P. G. Tetrahedron Lett. 1996, 37, 7577. (d) Hamachi, K.; Irie, R.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4979. (e) Kawasaki, K.; Katsuki, T. Tetrahedron 1997, 53, 6337. (f) Clark, J. S.; Tolhurst, K. F.; Taylor, M.; Swallow, S. J. Chem. Soc., Perkin Trans. 1 1998, 1167. (g) Sekar, G.; DattaGupta, A.; Singh, V. K. J. Org. Chem. 1998, 63, 2961. (h) Kohmura, Y.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3941. (i) Andrus, M. B.; Asgari, D. Tetrahedron 2000, 56, 5775. (j) Lee, S.Z.; Kwong, H.-L.; Chan, H.-L.; Choi, W.-W.; Ng, L.-Y. Tetrahedron: Asymmetry 2001, 12, 1007. (k) Andrus, M. B.; Zhou, Z. J. Am. Chem. Soc. 2002, 124, 8806. (l) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Tetrahedron Lett. 2002, 43, 3601. (m) Chelucci, G.; Iuliano, A.; Muroni, D. Saba, A. J. Mol. Catal. A 2003, 191, 29. For mechanistic issues in the nonasymmetric, Ru-catalyzed allylic oxidation, see: (m) Stultz, R. T.; Huynh, M. H. V.; Binstead, R. A.; Curry, M.; Meyer, T. J. J. Am. Chem. Soc. 2000, 122, 5984. For reviews, see: (n) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567. (o) Andrus, M. B.; Lashley, J. Tetrahedron 2002, 58, 845.
127. (a) Gokhale, A. S.; Minidis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831. (b) Andrus, M. A.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (c) Södergren, M. J.; Andersson,P. G. Tetrahedron Lett. 1996, 37, 7577. (d) Hamachi, K.; Irie, R.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4979. (e) Kawasaki, K.; Katsuki, T. Tetrahedron 1997, 53, 6337. (f) Clark, J. S.; Tolhurst, K. F.; Taylor, M.; Swallow, S. J. Chem. Soc., Perkin Trans. 1 1998, 1167. (g) Sekar, G.; DattaGupta, A.; Singh, V. K. J. Org. Chem. 1998, 63, 2961. (h) Kohmura, Y.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3941. (i) Andrus, M. B.; Asgari, D. Tetrahedron 2000, 56, 5775. (j) Lee, S.Z.; Kwong, H.-L.; Chan, H.-L.; Choi, W.-W.; Ng, L.-Y. Tetrahedron: Asymmetry 2001, 12, 1007. (k) Andrus, M. B.; Zhou, Z. J. Am. Chem. Soc. 2002, 124, 8806. (l) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Tetrahedron Lett. 2002, 43, 3601. (m) Chelucci, G.; Iuliano, A.; Muroni, D. Saba, A. J. Mol. Catal. A 2003, 191, 29. For mechanistic issues in the nonasymmetric, Ru-catalyzed allylic oxidation, see: (m) Stultz, R. T.; Huynh, M. H. V.; Binstead, R. A.; Curry, M.; Meyer, T. J. J. Am. Chem. Soc. 2000, 122, 5984. For reviews, see: (n) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567. (o) Andrus, M. B.; Lashley, J. Tetrahedron 2002, 58, 845.
128. (a) Gokhale, A. S.; Minidis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831. (b) Andrus, M. A.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (c) Södergren, M. J.; Andersson,P. G. Tetrahedron Lett. 1996, 37, 7577. (d) Hamachi, K.; Irie, R.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4979. (e) Kawasaki, K.; Katsuki, T. Tetrahedron 1997, 53, 6337. (f) Clark, J. S.; Tolhurst, K. F.; Taylor, M.; Swallow, S. J. Chem. Soc., Perkin Trans. 1 1998, 1167. (g) Sekar, G.; DattaGupta, A.; Singh, V. K. J. Org. Chem. 1998, 63, 2961. (h) Kohmura, Y.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3941. (i) Andrus, M. B.; Asgari, D. Tetrahedron 2000, 56, 5775. (j) Lee, S.Z.; Kwong, H.-L.; Chan, H.-L.; Choi, W.-W.; Ng, L.-Y. Tetrahedron: Asymmetry 2001, 12, 1007. (k) Andrus, M. B.; Zhou, Z. J. Am. Chem. Soc. 2002, 124, 8806. (l) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Tetrahedron Lett. 2002, 43, 3601. (m) Chelucci, G.; Iuliano, A.; Muroni, D. Saba, A. J. Mol. Catal. A 2003, 191, 29. For mechanistic issues in the nonasymmetric, Ru-catalyzed allylic oxidation, see: (m) Stultz, R. T.; Huynh, M. H. V.; Binstead, R. A.; Curry, M.; Meyer, T. J. J. Am. Chem. Soc. 2000, 122, 5984. For reviews, see: (n) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567. (o) Andrus, M. B.; Lashley, J. Tetrahedron 2002, 58, 845.
129. (a) Gokhale, A. S.; Minidis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831. (b) Andrus, M. A.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (c) Södergren, M. J.; Andersson,P. G. Tetrahedron Lett. 1996, 37, 7577. (d) Hamachi, K.; Irie, R.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4979. (e) Kawasaki, K.; Katsuki, T. Tetrahedron 1997, 53, 6337. (f) Clark, J. S.; Tolhurst, K. F.; Taylor, M.; Swallow, S. J. Chem. Soc., Perkin Trans. 1 1998, 1167. (g) Sekar, G.; DattaGupta, A.; Singh, V. K. J. Org. Chem. 1998, 63, 2961. (h) Kohmura, Y.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3941. (i) Andrus, M. B.; Asgari, D. Tetrahedron 2000, 56, 5775. (j) Lee, S.Z.; Kwong, H.-L.; Chan, H.-L.; Choi, W.-W.; Ng, L.-Y. Tetrahedron: Asymmetry 2001, 12, 1007. (k) Andrus, M. B.; Zhou, Z. J. Am. Chem. Soc. 2002, 124, 8806. (l) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Tetrahedron Lett. 2002, 43, 3601. (m) Chelucci, G.; Iuliano, A.; Muroni, D. Saba, A. J. Mol. Catal. A 2003, 191, 29. For mechanistic issues in the nonasymmetric, Ru-catalyzed allylic oxidation, see: (m) Stultz, R. T.; Huynh, M. H. V.; Binstead, R. A.; Curry, M.; Meyer, T. J. J. Am. Chem. Soc. 2000, 122, 5984. For reviews, see: (n) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567. (o) Andrus, M. B.; Lashley, J. Tetrahedron 2002, 58, 845.
130. (a) Gokhale, A. S.; Minidis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831. (b) Andrus, M. A.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (c) Södergren, M. J.; Andersson,P. G. Tetrahedron Lett. 1996, 37, 7577. (d) Hamachi, K.; Irie, R.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4979. (e) Kawasaki, K.; Katsuki, T. Tetrahedron 1997, 53, 6337. (f) Clark, J. S.; Tolhurst, K. F.; Taylor, M.; Swallow, S. J. Chem. Soc., Perkin Trans. 1 1998, 1167. (g) Sekar, G.; DattaGupta, A.; Singh, V. K. J. Org. Chem. 1998, 63, 2961. (h) Kohmura, Y.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3941. (i) Andrus, M. B.; Asgari, D. Tetrahedron 2000, 56, 5775. (j) Lee, S.Z.; Kwong, H.-L.; Chan, H.-L.; Choi, W.-W.; Ng, L.-Y. Tetrahedron: Asymmetry 2001, 12, 1007. (k) Andrus, M. B.; Zhou, Z. J. Am. Chem. Soc. 2002, 124, 8806. (l) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Tetrahedron Lett. 2002, 43, 3601. (m) Chelucci, G.; Iuliano, A.; Muroni, D. Saba, A. J. Mol. Catal. A 2003, 191, 29. For mechanistic issues in the nonasymmetric, Ru-catalyzed allylic oxidation, see: (m) Stultz, R. T.; Huynh, M. H. V.; Binstead, R. A.; Curry, M.; Meyer, T. J. J. Am. Chem. Soc. 2000, 122, 5984. For reviews, see: (n) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567. (o) Andrus, M. B.; Lashley, J. Tetrahedron 2002, 58, 845.
131. (a) Gokhale, A. S.; Minidis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831. (b) Andrus, M. A.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (c) Södergren, M. J.; Andersson,P. G. Tetrahedron Lett. 1996, 37, 7577. (d) Hamachi, K.; Irie, R.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4979. (e) Kawasaki, K.; Katsuki, T. Tetrahedron 1997, 53, 6337. (f) Clark, J. S.; Tolhurst, K. F.; Taylor, M.; Swallow, S. J. Chem. Soc., Perkin Trans. 1 1998, 1167. (g) Sekar, G.; DattaGupta, A.; Singh, V. K. J. Org. Chem. 1998, 63, 2961. (h) Kohmura, Y.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3941. (i) Andrus, M. B.; Asgari, D. Tetrahedron 2000, 56, 5775. (j) Lee, S.Z.; Kwong, H.-L.; Chan, H.-L.; Choi, W.-W.; Ng, L.-Y. Tetrahedron: Asymmetry 2001, 12, 1007. (k) Andrus, M. B.; Zhou, Z. J. Am. Chem. Soc. 2002, 124, 8806. (l) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Tetrahedron Lett. 2002, 43, 3601. (m) Chelucci, G.; Iuliano, A.; Muroni, D. Saba, A. J. Mol. Catal. A 2003, 191, 29. For mechanistic issues in the nonasymmetric, Ru-catalyzed allylic oxidation, see: (m) Stultz, R. T.; Huynh, M. H. V.; Binstead, R. A.; Curry, M.; Meyer, T. J. J. Am. Chem. Soc. 2000, 122, 5984. For reviews, see: (n) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567. (o) Andrus, M. B.; Lashley, J. Tetrahedron 2002, 58, 845.
132. (a) Gokhale, A. S.; Minidis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831. (b) Andrus, M. A.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (c) Södergren, M. J.; Andersson,P. G. Tetrahedron Lett. 1996, 37, 7577. (d) Hamachi, K.; Irie, R.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4979. (e) Kawasaki, K.; Katsuki, T. Tetrahedron 1997, 53, 6337. (f) Clark, J. S.; Tolhurst, K. F.; Taylor, M.; Swallow, S. J. Chem. Soc., Perkin Trans. 1 1998, 1167. (g) Sekar, G.; DattaGupta, A.; Singh, V. K. J. Org. Chem. 1998, 63, 2961. (h) Kohmura, Y.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3941. (i) Andrus, M. B.; Asgari, D. Tetrahedron 2000, 56, 5775. (j) Lee, S.Z.; Kwong, H.-L.; Chan, H.-L.; Choi, W.-W.; Ng, L.-Y. Tetrahedron: Asymmetry 2001, 12, 1007. (k) Andrus, M. B.; Zhou, Z. J. Am. Chem. Soc. 2002, 124, 8806. (l) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Tetrahedron Lett. 2002, 43, 3601. (m) Chelucci, G.; Iuliano, A.; Muroni, D. Saba, A. J. Mol. Catal. A 2003, 191, 29. For mechanistic issues in the nonasymmetric, Ru-catalyzed allylic oxidation, see: (m) Stultz, R. T.; Huynh, M. H. V.; Binstead, R. A.; Curry, M.; Meyer, T. J. J. Am. Chem. Soc. 2000, 122, 5984. For reviews, see: (n) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567. (o) Andrus, M. B.; Lashley, J. Tetrahedron 2002, 58, 845.
133. (a) Gokhale, A. S.; Minidis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831. (b) Andrus, M. A.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (c) Södergren, M. J.; Andersson,P. G. Tetrahedron Lett. 1996, 37, 7577. (d) Hamachi, K.; Irie, R.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4979. (e) Kawasaki, K.; Katsuki, T. Tetrahedron 1997, 53, 6337. (f) Clark, J. S.; Tolhurst, K. F.; Taylor, M.; Swallow, S. J. Chem. Soc., Perkin Trans. 1 1998, 1167. (g) Sekar, G.; DattaGupta, A.; Singh, V. K. J. Org. Chem. 1998, 63, 2961. (h) Kohmura, Y.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3941. (i) Andrus, M. B.; Asgari, D. Tetrahedron 2000, 56, 5775. (j) Lee, S.Z.; Kwong, H.-L.; Chan, H.-L.; Choi, W.-W.; Ng, L.-Y. Tetrahedron: Asymmetry 2001, 12, 1007. (k) Andrus, M. B.; Zhou, Z. J. Am. Chem. Soc. 2002, 124, 8806. (l) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Tetrahedron Lett. 2002, 43, 3601. (m) Chelucci, G.; Iuliano, A.; Muroni, D. Saba, A. J. Mol. Catal. A 2003, 191, 29. For mechanistic issues in the nonasymmetric, Ru-catalyzed allylic oxidation, see: (m) Stultz, R. T.; Huynh, M. H. V.; Binstead, R. A.; Curry, M.; Meyer, T. J. J. Am. Chem. Soc. 2000, 122, 5984. For reviews, see: (n) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567. (o) Andrus, M. B.; Lashley, J. Tetrahedron 2002, 58, 845.
134. (a) Gokhale, A. S.; Minidis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831. (b) Andrus, M. A.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (c) Södergren, M. J.; Andersson,P. G. Tetrahedron Lett. 1996, 37, 7577. (d) Hamachi, K.; Irie, R.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4979. (e) Kawasaki, K.; Katsuki, T. Tetrahedron 1997, 53, 6337. (f) Clark, J. S.; Tolhurst, K. F.; Taylor, M.; Swallow, S. J. Chem. Soc., Perkin Trans. 1 1998, 1167. (g) Sekar, G.; DattaGupta, A.; Singh, V. K. J. Org. Chem. 1998, 63, 2961. (h) Kohmura, Y.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3941. (i) Andrus, M. B.; Asgari, D. Tetrahedron 2000, 56, 5775. (j) Lee, S.Z.; Kwong, H.-L.; Chan, H.-L.; Choi, W.-W.; Ng, L.-Y. Tetrahedron: Asymmetry 2001, 12, 1007. (k) Andrus, M. B.; Zhou, Z. J. Am. Chem. Soc. 2002, 124, 8806. (l) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Tetrahedron Lett. 2002, 43, 3601. (m) Chelucci, G.; Iuliano, A.; Muroni, D. Saba, A. J. Mol. Catal. A 2003, 191, 29. For mechanistic issues in the nonasymmetric, Ru-catalyzed allylic oxidation, see: (m) Stultz, R. T.; Huynh, M. H. V.; Binstead, R. A.; Curry, M.; Meyer, T. J. J. Am. Chem. Soc. 2000, 122, 5984. For reviews, see: (n) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567. (o) Andrus, M. B.; Lashley, J. Tetrahedron 2002, 58, 845.
135. (a) Gokhale, A. S.; Minidis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831. (b) Andrus, M. A.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (c) Södergren, M. J.; Andersson,P. G. Tetrahedron Lett. 1996, 37, 7577. (d) Hamachi, K.; Irie, R.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4979. (e) Kawasaki, K.; Katsuki, T. Tetrahedron 1997, 53, 6337. (f) Clark, J. S.; Tolhurst, K. F.; Taylor, M.; Swallow, S. J. Chem. Soc., Perkin Trans. 1 1998, 1167. (g) Sekar, G.; DattaGupta, A.; Singh, V. K. J. Org. Chem. 1998, 63, 2961. (h) Kohmura, Y.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3941. (i) Andrus, M. B.; Asgari, D. Tetrahedron 2000, 56, 5775. (j) Lee, S.Z.; Kwong, H.-L.; Chan, H.-L.; Choi, W.-W.; Ng, L.-Y. Tetrahedron: Asymmetry 2001, 12, 1007. (k) Andrus, M. B.; Zhou, Z. J. Am. Chem. Soc. 2002, 124, 8806. (l) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Tetrahedron Lett. 2002, 43, 3601. (m) Chelucci, G.; Iuliano, A.; Muroni, D. Saba, A. J. Mol. Catal. A 2003, 191, 29. For mechanistic issues in the nonasymmetric, Ru-catalyzed allylic oxidation, see: (m) Stultz, R. T.; Huynh, M. H. V.; Binstead, R. A.; Curry, M.; Meyer, T. J. J. Am. Chem. Soc. 2000, 122, 5984. For reviews, see: (n) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567. (o) Andrus, M. B.; Lashley, J. Tetrahedron 2002, 58, 845.
136. (a) Gokhale, A. S.; Minidis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831. (b) Andrus, M. A.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (c) Södergren, M. J.; Andersson,P. G. Tetrahedron Lett. 1996, 37, 7577. (d) Hamachi, K.; Irie, R.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4979. (e) Kawasaki, K.; Katsuki, T. Tetrahedron 1997, 53, 6337. (f) Clark, J. S.; Tolhurst, K. F.; Taylor, M.; Swallow, S. J. Chem. Soc., Perkin Trans. 1 1998, 1167. (g) Sekar, G.; DattaGupta, A.; Singh, V. K. J. Org. Chem. 1998, 63, 2961. (h) Kohmura, Y.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3941. (i) Andrus, M. B.; Asgari, D. Tetrahedron 2000, 56, 5775. (j) Lee, S.Z.; Kwong, H.-L.; Chan, H.-L.; Choi, W.-W.; Ng, L.-Y. Tetrahedron: Asymmetry 2001, 12, 1007. (k) Andrus, M. B.; Zhou, Z. J. Am. Chem. Soc. 2002, 124, 8806. (l) Chelucci, G.; Loriga, G.; Murineddu, G.; Pinna, G. A. Tetrahedron Lett. 2002, 43, 3601. (m) Chelucci, G.; Iuliano, A.; Muroni, D. Saba, A. J. Mol. Catal. A 2003, 191, 29. For mechanistic issues in the nonasymmetric, Ru-catalyzed allylic oxidation, see: (m) Stultz, R. T.; Huynh, M. H. V.; Binstead, R. A.; Curry, M.; Meyer, T. J. J. Am. Chem. Soc. 2000, 122, 5984. For reviews, see: (n) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567. (o) Andrus, M. B.; Lashley, J. Tetrahedron 2002, 58, 845.
137. 46k However, the conversions in those cases were rather low, so that the reaction would better be described as substoichiometric rather than catalytic.
138. 46
139. At -20 °C, the reaction of cycloheptene proved to be extramely slow and the product was not analyzed because of low conversion.
140. In principle, the quasi-enantiomeric ligands 3 and 4 should exhibit practically identical levels of enantioselectivities. The lower enantioselectivity observed for 3 (compare entries 10 and 12) apparently originates from its lower enantiopurity (93% ee).
141. In the presence of molecular sieves, the oxidation of cyclohexene takes 26 h (74% yield) rather than 30 min, while the enantioselectivity (48% ee) remains unchanged (compare with Table 1, entry 3). At 0 °C, the addition of molecular sieves slows the reaction from 5 h to 7 days (51% yield), leaving the enantioselectivity (53% ee) intact again (compare with Table 1, entry 5). The actual nature of the effect of water is unknown. It can be tentatively attributed to a weak cordination to Cu, which may accelerate the departure of the product from Cu, allowing it to enter the next catalytic cycle. For similar observations of the water effect, see the following: (a) Mikami, K.; Kotera, O.; Motoyama, Y.; Sajaguchi, H. Synlett 1995, 975. (b) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281. (c) Hatano, M.; Terada, M.; Mikami, K. Angew. Chem., Int. Ed. 2001, 40, 249. (d) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936. (e) Evans, D. A.; Johnson, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635. (f) Evans, D. A.; Miller, S. J.; Lectka, T.; von Matt, P. J. Am. Chem. Soc. 1999, 121, 7559. (g) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; von Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos K. R. J. Am. Chem. Soc. 1999, 121, 7582. (h) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669. For an overview of the water effects in metal-catalyzed reactions, see: (i) Ribe, S.; Wipf, P. Chem. Commun. 2001, 299.
142. In the presence of molecular sieves, the oxidation of cyclohexene takes 26 h (74% yield) rather than 30 min, while the enantioselectivity (48% ee) remains unchanged (compare with Table 1, entry 3). At 0 °C, the addition of molecular sieves slows the reaction from 5 h to 7 days (51% yield), leaving the enantioselectivity (53% ee) intact again (compare with Table 1, entry 5). The actual nature of the effect of water is unknown. It can be tentatively attributed to a weak cordination to Cu, which may accelerate the departure of the product from Cu, allowing it to enter the next catalytic cycle. For similar observations of the water effect, see the following: (a) Mikami, K.; Kotera, O.; Motoyama, Y.; Sajaguchi, H. Synlett 1995, 975. (b) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281. (c) Hatano, M.; Terada, M.; Mikami, K. Angew. Chem., Int. Ed. 2001, 40, 249. (d) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936. (e) Evans, D. A.; Johnson, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635. (f) Evans, D. A.; Miller, S. J.; Lectka, T.; von Matt, P. J. Am. Chem. Soc. 1999, 121, 7559. (g) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; von Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos K. R. J. Am. Chem. Soc. 1999, 121, 7582. (h) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669. For an overview of the water effects in metal-catalyzed reactions, see: (i) Ribe, S.; Wipf, P. Chem. Commun. 2001, 299.
143. In the presence of molecular sieves, the oxidation of cyclohexene takes 26 h (74% yield) rather than 30 min, while the enantioselectivity (48% ee) remains unchanged (compare with Table 1, entry 3). At 0 °C, the addition of molecular sieves slows the reaction from 5 h to 7 days (51% yield), leaving the enantioselectivity (53% ee) intact again (compare with Table 1, entry 5). The actual nature of the effect of water is unknown. It can be tentatively attributed to a weak cordination to Cu, which may accelerate the departure of the product from Cu, allowing it to enter the next catalytic cycle. For similar observations of the water effect, see the following: (a) Mikami, K.; Kotera, O.; Motoyama, Y.; Sajaguchi, H. Synlett 1995, 975. (b) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281. (c) Hatano, M.; Terada, M.; Mikami, K. Angew. Chem., Int. Ed. 2001, 40, 249. (d) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936. (e) Evans, D. A.; Johnson, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635. (f) Evans, D. A.; Miller, S. J.; Lectka, T.; von Matt, P. J. Am. Chem. Soc. 1999, 121, 7559. (g) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; von Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos K. R. J. Am. Chem. Soc. 1999, 121, 7582. (h) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669. For an overview of the water effects in metal-catalyzed reactions, see: (i) Ribe, S.; Wipf, P. Chem. Commun. 2001, 299.
144. In the presence of molecular sieves, the oxidation of cyclohexene takes 26 h (74% yield) rather than 30 min, while the enantioselectivity (48% ee) remains unchanged (compare with Table 1, entry 3). At 0 °C, the addition of molecular sieves slows the reaction from 5 h to 7 days (51% yield), leaving the enantioselectivity (53% ee) intact again (compare with Table 1, entry 5). The actual nature of the effect of water is unknown. It can be tentatively attributed to a weak cordination to Cu, which may accelerate the departure of the product from Cu, allowing it to enter the next catalytic cycle. For similar observations of the water effect, see the following: (a) Mikami, K.; Kotera, O.; Motoyama, Y.; Sajaguchi, H. Synlett 1995, 975. (b) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281. (c) Hatano, M.; Terada, M.; Mikami, K. Angew. Chem., Int. Ed. 2001, 40, 249. (d) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936. (e) Evans, D. A.; Johnson, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635. (f) Evans, D. A.; Miller, S. J.; Lectka, T.; von Matt, P. J. Am. Chem. Soc. 1999, 121, 7559. (g) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; von Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos K. R. J. Am. Chem. Soc. 1999, 121, 7582. (h) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669. For an overview of the water effects in metal-catalyzed reactions, see: (i) Ribe, S.; Wipf, P. Chem. Commun. 2001, 299.
145. In the presence of molecular sieves, the oxidation of cyclohexene takes 26 h (74% yield) rather than 30 min, while the enantioselectivity (48% ee) remains unchanged (compare with Table 1, entry 3). At 0 °C, the addition of molecular sieves slows the reaction from 5 h to 7 days (51% yield), leaving the enantioselectivity (53% ee) intact again (compare with Table 1, entry 5). The actual nature of the effect of water is unknown. It can be tentatively attributed to a weak cordination to Cu, which may accelerate the departure of the product from Cu, allowing it to enter the next catalytic cycle. For similar observations of the water effect, see the following: (a) Mikami, K.; Kotera, O.; Motoyama, Y.; Sajaguchi, H. Synlett 1995, 975. (b) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281. (c) Hatano, M.; Terada, M.; Mikami, K. Angew. Chem., Int. Ed. 2001, 40, 249. (d) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936. (e) Evans, D. A.; Johnson, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635. (f) Evans, D. A.; Miller, S. J.; Lectka, T.; von Matt, P. J. Am. Chem. Soc. 1999, 121, 7559. (g) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; von Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos K. R. J. Am. Chem. Soc. 1999, 121, 7582. (h) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669. For an overview of the water effects in metal-catalyzed reactions, see: (i) Ribe, S.; Wipf, P. Chem. Commun. 2001, 299.
146. In the presence of molecular sieves, the oxidation of cyclohexene takes 26 h (74% yield) rather than 30 min, while the enantioselectivity (48% ee) remains unchanged (compare with Table 1, entry 3). At 0 °C, the addition of molecular sieves slows the reaction from 5 h to 7 days (51% yield), leaving the enantioselectivity (53% ee) intact again (compare with Table 1, entry 5). The actual nature of the effect of water is unknown. It can be tentatively attributed to a weak cordination to Cu, which may accelerate the departure of the product from Cu, allowing it to enter the next catalytic cycle. For similar observations of the water effect, see the following: (a) Mikami, K.; Kotera, O.; Motoyama, Y.; Sajaguchi, H. Synlett 1995, 975. (b) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281. (c) Hatano, M.; Terada, M.; Mikami, K. Angew. Chem., Int. Ed. 2001, 40, 249. (d) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936. (e) Evans, D. A.; Johnson, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635. (f) Evans, D. A.; Miller, S. J.; Lectka, T.; von Matt, P. J. Am. Chem. Soc. 1999, 121, 7559. (g) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; von Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos K. R. J. Am. Chem. Soc. 1999, 121, 7582. (h) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669. For an overview of the water effects in metal-catalyzed reactions, see: (i) Ribe, S.; Wipf, P. Chem. Commun. 2001, 299.
147. In the presence of molecular sieves, the oxidation of cyclohexene takes 26 h (74% yield) rather than 30 min, while the enantioselectivity (48% ee) remains unchanged (compare with Table 1, entry 3). At 0 °C, the addition of molecular sieves slows the reaction from 5 h to 7 days (51% yield), leaving the enantioselectivity (53% ee) intact again (compare with Table 1, entry 5). The actual nature of the effect of water is unknown. It can be tentatively attributed to a weak cordination to Cu, which may accelerate the departure of the product from Cu, allowing it to enter the next catalytic cycle. For similar observations of the water effect, see the following: (a) Mikami, K.; Kotera, O.; Motoyama, Y.; Sajaguchi, H. Synlett 1995, 975. (b) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281. (c) Hatano, M.; Terada, M.; Mikami, K. Angew. Chem., Int. Ed. 2001, 40, 249. (d) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936. (e) Evans, D. A.; Johnson, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635. (f) Evans, D. A.; Miller, S. J.; Lectka, T.; von Matt, P. J. Am. Chem. Soc. 1999, 121, 7559. (g) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; von Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos K. R. J. Am. Chem. Soc. 1999, 121, 7582. (h) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669. For an overview of the water effects in metal-catalyzed reactions, see: (i) Ribe, S.; Wipf, P. Chem. Commun. 2001, 299.
148. In the presence of molecular sieves, the oxidation of cyclohexene takes 26 h (74% yield) rather than 30 min, while the enantioselectivity (48% ee) remains unchanged (compare with Table 1, entry 3). At 0 °C, the addition of molecular sieves slows the reaction from 5 h to 7 days (51% yield), leaving the enantioselectivity (53% ee) intact again (compare with Table 1, entry 5). The actual nature of the effect of water is unknown. It can be tentatively attributed to a weak cordination to Cu, which may accelerate the departure of the product from Cu, allowing it to enter the next catalytic cycle. For similar observations of the water effect, see the following: (a) Mikami, K.; Kotera, O.; Motoyama, Y.; Sajaguchi, H. Synlett 1995, 975. (b) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281. (c) Hatano, M.; Terada, M.; Mikami, K. Angew. Chem., Int. Ed. 2001, 40, 249. (d) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936. (e) Evans, D. A.; Johnson, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635. (f) Evans, D. A.; Miller, S. J.; Lectka, T.; von Matt, P. J. Am. Chem. Soc. 1999, 121, 7559. (g) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; von Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos K. R. J. Am. Chem. Soc. 1999, 121, 7582. (h) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669. For an overview of the water effects in metal-catalyzed reactions, see: (i) Ribe, S.; Wipf, P. Chem. Commun. 2001, 299.
149. In the presence of molecular sieves, the oxidation of cyclohexene takes 26 h (74% yield) rather than 30 min, while the enantioselectivity (48% ee) remains unchanged (compare with Table 1, entry 3). At 0 °C, the addition of molecular sieves slows the reaction from 5 h to 7 days (51% yield), leaving the enantioselectivity (53% ee) intact again (compare with Table 1, entry 5). The actual nature of the effect of water is unknown. It can be tentatively attributed to a weak cordination to Cu, which may accelerate the departure of the product from Cu, allowing it to enter the next catalytic cycle. For similar observations of the water effect, see the following: (a) Mikami, K.; Kotera, O.; Motoyama, Y.; Sajaguchi, H. Synlett 1995, 975. (b) Terada, M.; Matsumoto, Y.; Nakamura, Y.; Mikami, K. Chem. Commun. 1997, 281. (c) Hatano, M.; Terada, M.; Mikami, K. Angew. Chem., Int. Ed. 2001, 40, 249. (d) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936. (e) Evans, D. A.; Johnson, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635. (f) Evans, D. A.; Miller, S. J.; Lectka, T.; von Matt, P. J. Am. Chem. Soc. 1999, 121, 7559. (g) Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; von Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos K. R. J. Am. Chem. Soc. 1999, 121, 7582. (h) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669. For an overview of the water effects in metal-catalyzed reactions, see: (i) Ribe, S.; Wipf, P. Chem. Commun. 2001, 299.
150. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
151. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee,
152. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
153. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
154. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
155. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
156. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
157. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
158. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
159. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
160. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
161. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
162. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
163. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
164. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
165. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
166. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
167. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
168. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
169. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj,
170. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
171. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
172. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
173. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
174. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
175. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
176. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
177. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
178. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
179. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
180. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
181. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
182. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
183. For an overview of asymmetric, metal-catalyzed cyclopropanation, see, for example, ref 1 and the following: (a) Aratani, T. Pure Appl. Chem. 1985, 57, 1839. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; J. Wiley: New York, 1998. For selected, recent examples, seethe following. Cu: (c) Frischi, H.; Leuteneggar, U.; Pfaltz, A. Helv.Chim. Acta 1988, 71, 1553 and references therein. (d) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005. (e) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373. (f) Müler, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. (g) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726. (h) Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 430. (i) Schumacher,R.; Dammast, F.; Reissing, H. U. Chem. Eur. J. 1997, 3, 614. (j) Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518. (k) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007 and references therein. (k) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron 1999, 55, 649. (l) Burguette, M. I.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Herrerías, C. I.; Luis, S. V.; Mayoral, V. A. J. Org. Chem. 2001, 66, 8893. (m) Fraile, J. M.; García, J. I.; Martinez-Merino, V.; Mayoral, V. A.; Savatella, L. J. Am. Chem. Soc. 2001, 123, 7616. (n) Che, C.-M.; Kwong, H.-L.; Che, W.-C.; Cheng, K.-F.; Lee, W.-S.; Yu, H.-S.; Yeung, C. T.; Cheung, K.-K. Eur. J. Inorg. Chem. 2002, 1456. (o) Wong, W.-L.; Lee, W.-S.; Kwong, H.-L. Tetrahedron: Asymmetry 2002, 13, 1485. (p) Rasmussen, T.; Jensen, J. F.; Østergaard, N.; Tanner, D.; Ziegler, T.; Norrby, P.-O. Chem. Eur. J. 2002, 8, 177. Co: (q) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719. (r) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345. (s) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647 and references therein. (t) Ikeno, T.; Iwakura, I.; Yabushita, S.; Yamada, T. Org. Lett. 2002, 4, 517. (u) Ikeno, T.; Iwakura, I.; Yamada, T. J. Am. Chem. Soc. 2002, 124, 15152. Ru: ref 52s and the following: (v) Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119. (w) Cornejo, A.; Fraile, J. M.; García, J. I.; García-Verungo, E.; Gil, M. J.; Legarreta, G.; Luis, S. V.; Martínez-Merino, V.; Mayoral, V. A. Org. Lett. 2002, 4, 3927. Rh: (x) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919. (y) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595. (z) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 3, 3317. (aa) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667. (bb) Nagashima, T.; Davies, H. M. L. Org. Lett. 2002, 4, 1989. (cc) Chelucci, G.; Saba, A.; Soccolini, F.; Vignola, D. J. Mol. Catal. 2002, 178, 27. (dd) Doyle, M. P.; Forbes, C. D. Chem. Rev. 1998, 98, 911. Fe: (ee) Du. G.; Andrioletti, B.; Rose, E.; Woo, L. K. Organometallics 2002, 21, 4490. Zn/Ti (asymmetric Simmons-Smith addition): (ff) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168. (gg) Imai, N.; Nomura, T.; Yamamoto, S.; Ninomiya, Y.; Nokami, J. Tetrahedron: Asymmetry 2002, 13, 2433.
184. For the recently developed bipyridine-type complexes that catalyze cyclopropanation, see, for example, refs 4g and 6k,1 and the following: (a) Ito, K.; Tabuchi, S.; Katsuki, T. Synlett 1992, 575. (b) Ito, K.; Katsuki, T. Tetrahedron Lett. 1993, 34, 2661. (c) Ito, K.; Katsuki, T. Synlett 1993, 638.
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