Design of a new class of chiral C2-symmetric dipyridylmethane ligands and their application in asymmetric catalysis

Tetrahedron Letters

Volumn 43, Issue 47, 2002, Pages 8599-8602

  Chelucci, Giorgio ^a   Loriga, Giovanni ^a   Murineddu, Gabriele ^a   Pinna, Gerard A ^a  

^a UNIVERSITY OF SASSARI   (Italy)

Author keywords

Allylic alkylation; Cyclopropanation; Dipyridylmethane ligands; Enantioselectivity

Indexed keywords

ACETIC ACID DERIVATIVE; BIPYRIDINE DERIVATIVE; COPPER; DIAZOACETIC ACID ETHYL ESTER; LIGAND; MALONIC ACID DERIVATIVE; PALLADIUM; STYRENE; TERPENE DERIVATIVE;

ALKYLATION; AROMATIZATION; ARTICLE; ASYMMETRIC CATALYSIS; AZAANNELLATION; CHEMICAL REACTION; CHIRALITY; CYCLOPROPANATION; ENANTIOSELECTIVITY;

EID: 0037131747     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02066-X     Document Type: Article

References (40)

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11. For on an overview of the syntheses and applications in asymmetric catalysis of chiral pyridine ligands, see: (a) Chelucci, G.; Thummel, R. P. Chem. Rev. 2002, 102, 3129-3170. For the most recent reports, see: (b) Malkov, A. V.; Baxandale, I. R.; Bella, M.; Langer, V.; Fawcett, J.; Russell, D. R.; Mansfield, D. J.; Valko, M.; Kocovsky, P. Organometallics 2001, 20, 673; (c) Malkov, A. V.; Bella, M.; Langer, V.; Kocovsky, P. Org. Lett. 2000, 2, 3047; (d) Wong, H. L.; Tian, Y.; Chan, K. S. Tetrahedron Lett. 2000, 41, 7723; (e) Rios, R.; Liang, J.; Lo, M. M.-C.; Fu, G. C. Chem. Commun. 2000, 377; (f) Chelucci, G.; Culeddu, N.; Saba, A.; Valenti, R. Tetrahedron: Asymmetry 1999, 10, 3537; (g) Fletcher, N. C.; Keene, F. R.; Ziegler, M.; Stoeckli-Evans, H.; Viebrock, H.; von Zelewsky, A. Helv. Chim. Acta 1996, 79, 119; (h) Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron 1996, 3905.
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13. For on an overview of the syntheses and applications in asymmetric catalysis of chiral pyridine ligands, see: (a) Chelucci, G.; Thummel, R. P. Chem. Rev. 2002, 102, 3129-3170. For the most recent reports, see: (b) Malkov, A. V.; Baxandale, I. R.; Bella, M.; Langer, V.; Fawcett, J.; Russell, D. R.; Mansfield, D. J.; Valko, M.; Kocovsky, P. Organometallics 2001, 20, 673; (c) Malkov, A. V.; Bella, M.; Langer, V.; Kocovsky, P. Org. Lett. 2000, 2, 3047; (d) Wong, H. L.; Tian, Y.; Chan, K. S. Tetrahedron Lett. 2000, 41, 7723; (e) Rios, R.; Liang, J.; Lo, M. M.-C.; Fu, G. C. Chem. Commun. 2000, 377; (f) Chelucci, G.; Culeddu, N.; Saba, A.; Valenti, R. Tetrahedron: Asymmetry 1999, 10, 3537; (g) Fletcher, N. C.; Keene, F. R.; Ziegler, M.; Stoeckli-Evans, H.; Viebrock, H.; von Zelewsky, A. Helv. Chim. Acta 1996, 79, 119; (h) Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron 1996, 3905.
14. For on an overview of the syntheses and applications in asymmetric catalysis of chiral pyridine ligands, see: (a) Chelucci, G.; Thummel, R. P. Chem. Rev. 2002, 102, 3129-3170. For the most recent reports, see: (b) Malkov, A. V.; Baxandale, I. R.; Bella, M.; Langer, V.; Fawcett, J.; Russell, D. R.; Mansfield, D. J.; Valko, M.; Kocovsky, P. Organometallics 2001, 20, 673; (c) Malkov, A. V.; Bella, M.; Langer, V.; Kocovsky, P. Org. Lett. 2000, 2, 3047; (d) Wong, H. L.; Tian, Y.; Chan, K. S. Tetrahedron Lett. 2000, 41, 7723; (e) Rios, R.; Liang, J.; Lo, M. M.-C.; Fu, G. C. Chem. Commun. 2000, 377; (f) Chelucci, G.; Culeddu, N.; Saba, A.; Valenti, R. Tetrahedron: Asymmetry 1999, 10, 3537; (g) Fletcher, N. C.; Keene, F. R.; Ziegler, M.; Stoeckli-Evans, H.; Viebrock, H.; von Zelewsky, A. Helv. Chim. Acta 1996, 79, 119; (h) Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron 1996, 3905.
15. For on an overview of the syntheses and applications in asymmetric catalysis of chiral pyridine ligands, see: (a) Chelucci, G.; Thummel, R. P. Chem. Rev. 2002, 102, 3129-3170. For the most recent reports, see: (b) Malkov, A. V.; Baxandale, I. R.; Bella, M.; Langer, V.; Fawcett, J.; Russell, D. R.; Mansfield, D. J.; Valko, M.; Kocovsky, P. Organometallics 2001, 20, 673; (c) Malkov, A. V.; Bella, M.; Langer, V.; Kocovsky, P. Org. Lett. 2000, 2, 3047; (d) Wong, H. L.; Tian, Y.; Chan, K. S. Tetrahedron Lett. 2000, 41, 7723; (e) Rios, R.; Liang, J.; Lo, M. M.-C.; Fu, G. C. Chem. Commun. 2000, 377; (f) Chelucci, G.; Culeddu, N.; Saba, A.; Valenti, R. Tetrahedron: Asymmetry 1999, 10, 3537; (g) Fletcher, N. C.; Keene, F. R.; Ziegler, M.; Stoeckli-Evans, H.; Viebrock, H.; von Zelewsky, A. Helv. Chim. Acta 1996, 79, 119; (h) Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron 1996, 3905.
16. For on an overview of the syntheses and applications in asymmetric catalysis of chiral pyridine ligands, see: (a) Chelucci, G.; Thummel, R. P. Chem. Rev. 2002, 102, 3129-3170. For the most recent reports, see: (b) Malkov, A. V.; Baxandale, I. R.; Bella, M.; Langer, V.; Fawcett, J.; Russell, D. R.; Mansfield, D. J.; Valko, M.; Kocovsky, P. Organometallics 2001, 20, 673; (c) Malkov, A. V.; Bella, M.; Langer, V.; Kocovsky, P. Org. Lett. 2000, 2, 3047; (d) Wong, H. L.; Tian, Y.; Chan, K. S. Tetrahedron Lett. 2000, 41, 7723; (e) Rios, R.; Liang, J.; Lo, M. M.-C.; Fu, G. C. Chem. Commun. 2000, 377; (f) Chelucci, G.; Culeddu, N.; Saba, A.; Valenti, R. Tetrahedron: Asymmetry 1999, 10, 3537; (g) Fletcher, N. C.; Keene, F. R.; Ziegler, M.; Stoeckli-Evans, H.; Viebrock, H.; von Zelewsky, A. Helv. Chim. Acta 1996, 79, 119; (h) Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron 1996, 3905.
17. For on an overview of the syntheses and applications in asymmetric catalysis of chiral pyridine ligands, see: (a) Chelucci, G.; Thummel, R. P. Chem. Rev. 2002, 102, 3129-3170. For the most recent reports, see: (b) Malkov, A. V.; Baxandale, I. R.; Bella, M.; Langer, V.; Fawcett, J.; Russell, D. R.; Mansfield, D. J.; Valko, M.; Kocovsky, P. Organometallics 2001, 20, 673; (c) Malkov, A. V.; Bella, M.; Langer, V.; Kocovsky, P. Org. Lett. 2000, 2, 3047; (d) Wong, H. L.; Tian, Y.; Chan, K. S. Tetrahedron Lett. 2000, 41, 7723; (e) Rios, R.; Liang, J.; Lo, M. M.-C.; Fu, G. C. Chem. Commun. 2000, 377; (f) Chelucci, G.; Culeddu, N.; Saba, A.; Valenti, R. Tetrahedron: Asymmetry 1999, 10, 3537; (g) Fletcher, N. C.; Keene, F. R.; Ziegler, M.; Stoeckli-Evans, H.; Viebrock, H.; von Zelewsky, A. Helv. Chim. Acta 1996, 79, 119; (h) Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron 1996, 3905.
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34. 20
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37. 2 (2.5 mL) was added dropwise over a period of 2 h and then the mixture was stirred for 16 h. The solvent was evaporated under vacuum and the residue was purified by column chromatography on silica gel (hexane/ethyl acetate=15/1) to afford a mixture of ethyl trans- and cis-2-phenyl-cyclopropane-1-carboxylates as colorless oil. The trans/cis ratio and the ee were determined by GC analysis on a diethyl-t-butylsilyl β-cyclodextrin capillary column 25 m×0.25 mm operated at 60°C for 5 min, then programmed at 3°C/min to 160°C. [Retention times: 33.2 (1S,2S) and 33.5 (1R,2R) min for trans 20; retention times: 31.4 (1R,2S) and 31.8 (1S,2R) min for cis 21.].
38. The trans- and cis-cyclopropane ratios recorded for ligands 6, 9 and 11 were 63/37, 63/37 and 69/31, respectively.
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