C2-symmetric diphosphine ligands with only the planar chirality of ferrocene for the palladium-catalyzed asymmetric allylic alkylation

Journal of Organic Chemistry

Volumn 64, Issue 17, 1999, Pages 6247-6251

  Zhang, Wanbin ^a   Shimanuki, Takashi ^a   Kida, Toshiyuki ^a   Nakatsuji, Yohji ^a   Ikeda, Isao ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,1' BIS(DIPHENYLPHOSPHINO) 2,2' BIS(OXAZOLINYL)FERROCENE; 1,3 DIPHENYLPROP 2 EN 1 YL ACETATE; ACETIC ACID DERIVATIVE; ALLYL COMPOUND; CYCLOHEX 2 EN 1 YL ACETATE; FERROCENE DERIVATIVE; LIGAND; MALONIC ACID DERIVATIVE; MALONIC ACID DIMETHYL ESTER; OXAZOLINE DERIVATIVE; PALLADIUM; PHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHIRALITY; DIASTEREOISOMER; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY; SYNTHESIS;

EID: 0033588130     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9902998     Document Type: Article

References (75)

1. (a) Rajanbabu, T. V.; Casalnuovo, A. L. J. Am. Chem. Soc. 1996, 118, 6325-6326.
2. (b) Reetz, M. T.; Beuttenmuller, E. W.; Goddard, R. Tetrahedron Lett. 1997, 38, 3211-3214.
3. (c) Zhu, G.; Cao, P.; Jiang, Q.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 1799-1800.
4. (d) Pye, J. P.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207-6208.
5. (e) Pye, P. J.; Rossen, K.; Reamer, R. A.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1998, 39, 4441-4444.
6. (f) Jiang, Q.; Jiang, Y.; Xiao, D.; Cao, P.; Zhang, X. Angew. Chem., Int. Ed. Engl. 1998, 37, 1100-1103.
7. For reviews, see: (a) Hayashi, T. In Ferrocenes; Togni, A., Hayashi, T., Eds., VCH: Weinheim, 1995; pp 105-142. (b) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377-2407. For recent examples, see: (c) Richards, C. J.; Mulvaney, A. W. Tetrahedron: Asymmetry 1996, 7, 1119-1130. (d) Nishibayashi, Y.; Segawa, K.; Arikawa, Y.; Ohe, K.; Hidai, M.; Uemura, S. J. Organomet. Chem. 1997, 546-547, 381-398. (e) Sammakia, T.; Stangeland, E. L. J. Org. Chem. 1997, 62, 6104-6105. (f) Enders, D.; Peters, R.; Lochtman, R.; Runsink, J. Synlett 1997, 1462-1464. (g) Lagneau, N. M.; Chen, Y.; Robben, P. M.; Sin, H.-S.; Takasu, K.; Chen, J.-S.; Robinson, P. D.; Hua, D. H. Tetrahedron 1997, 54, 7301-7334. (h) Chesney, A.; Bryce, M.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Synthesis 1998, 413-416. (i) Schwink, L.; Knochel, P. Chem. Eur. J. 1998, 4, 950-968. (j) Riant, O.; Argouarch, G.; Guillaneux, D.; Samuel, O.; Kagan, H. B. J. Org. Chem. 1998, 63, 3511-3514. (k) Bolm, C.; Muniz-Fernandez, K.; Seger, A.; Raabe, G.; Gunther, K. J. Org. Chem. 1998, 63, 7860-7867. (l) Torre, F. G.; Jalon, F. A.; Lopez-Agenjo, A.; Manzano, B. R.; Rodriguez, A.; Sturm, T.; Weissensteiner, W.; Martinez-Ripoll, M. Organometallics 1998, 17, 4634-4644.
8. For reviews, see: (a) Hayashi, T. In Ferrocenes; Togni, A., Hayashi, T., Eds., VCH: Weinheim, 1995; pp 105-142. (b) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377-2407. For recent examples, see: (c) Richards, C. J.; Mulvaney, A. W. Tetrahedron: Asymmetry 1996, 7, 1119-1130. (d) Nishibayashi, Y.; Segawa, K.; Arikawa, Y.; Ohe, K.; Hidai, M.; Uemura, S. J. Organomet. Chem. 1997, 546-547, 381-398. (e) Sammakia, T.; Stangeland, E. L. J. Org. Chem. 1997, 62, 6104-6105. (f) Enders, D.; Peters, R.; Lochtman, R.; Runsink, J. Synlett 1997, 1462-1464. (g) Lagneau, N. M.; Chen, Y.; Robben, P. M.; Sin, H.-S.; Takasu, K.; Chen, J.-S.; Robinson, P. D.; Hua, D. H. Tetrahedron 1997, 54, 7301-7334. (h) Chesney, A.; Bryce, M.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Synthesis 1998, 413-416. (i) Schwink, L.; Knochel, P. Chem. Eur. J. 1998, 4, 950-968. (j) Riant, O.; Argouarch, G.; Guillaneux, D.; Samuel, O.; Kagan, H. B. J. Org. Chem. 1998, 63, 3511-3514. (k) Bolm, C.; Muniz-Fernandez, K.; Seger, A.; Raabe, G.; Gunther, K. J. Org. Chem. 1998, 63, 7860-7867. (l) Torre, F. G.; Jalon, F. A.; Lopez-Agenjo, A.; Manzano, B. R.; Rodriguez, A.; Sturm, T.; Weissensteiner, W.; Martinez-Ripoll, M. Organometallics 1998, 17, 4634-4644.
9. For reviews, see: (a) Hayashi, T. In Ferrocenes; Togni, A., Hayashi, T., Eds., VCH: Weinheim, 1995; pp 105-142. (b) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377-2407. For recent examples, see: (c) Richards, C. J.; Mulvaney, A. W. Tetrahedron: Asymmetry 1996, 7, 1119-1130. (d) Nishibayashi, Y.; Segawa, K.; Arikawa, Y.; Ohe, K.; Hidai, M.; Uemura, S. J. Organomet. Chem. 1997, 546-547, 381-398. (e) Sammakia, T.; Stangeland, E. L. J. Org. Chem. 1997, 62, 6104-6105. (f) Enders, D.; Peters, R.; Lochtman, R.; Runsink, J. Synlett 1997, 1462-1464. (g) Lagneau, N. M.; Chen, Y.; Robben, P. M.; Sin, H.-S.; Takasu, K.; Chen, J.-S.; Robinson, P. D.; Hua, D. H. Tetrahedron 1997, 54, 7301-7334. (h) Chesney, A.; Bryce, M.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Synthesis 1998, 413-416. (i) Schwink, L.; Knochel, P. Chem. Eur. J. 1998, 4, 950-968. (j) Riant, O.; Argouarch, G.; Guillaneux, D.; Samuel, O.; Kagan, H. B. J. Org. Chem. 1998, 63, 3511-3514. (k) Bolm, C.; Muniz-Fernandez, K.; Seger, A.; Raabe, G.; Gunther, K. J. Org. Chem. 1998, 63, 7860-7867. (l) Torre, F. G.; Jalon, F. A.; Lopez-Agenjo, A.; Manzano, B. R.; Rodriguez, A.; Sturm, T.; Weissensteiner, W.; Martinez-Ripoll, M. Organometallics 1998, 17, 4634-4644.
10. For reviews, see: (a) Hayashi, T. In Ferrocenes; Togni, A., Hayashi, T., Eds., VCH: Weinheim, 1995; pp 105-142. (b) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377-2407. For recent examples, see: (c) Richards, C. J.; Mulvaney, A. W. Tetrahedron: Asymmetry 1996, 7, 1119-1130. (d) Nishibayashi, Y.; Segawa, K.; Arikawa, Y.; Ohe, K.; Hidai, M.; Uemura, S. J. Organomet. Chem. 1997, 546-547, 381-398. (e) Sammakia, T.; Stangeland, E. L. J. Org. Chem. 1997, 62, 6104-6105. (f) Enders, D.; Peters, R.; Lochtman, R.; Runsink, J. Synlett 1997, 1462-1464. (g) Lagneau, N. M.; Chen, Y.; Robben, P. M.; Sin, H.-S.; Takasu, K.; Chen, J.-S.; Robinson, P. D.; Hua, D. H. Tetrahedron 1997, 54, 7301-7334. (h) Chesney, A.; Bryce, M.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Synthesis 1998, 413-416. (i) Schwink, L.; Knochel, P. Chem. Eur. J. 1998, 4, 950-968. (j) Riant, O.; Argouarch, G.; Guillaneux, D.; Samuel, O.; Kagan, H. B. J. Org. Chem. 1998, 63, 3511-3514. (k) Bolm, C.; Muniz-Fernandez, K.; Seger, A.; Raabe, G.; Gunther, K. J. Org. Chem. 1998, 63, 7860-7867. (l) Torre, F. G.; Jalon, F. A.; Lopez-Agenjo, A.; Manzano, B. R.; Rodriguez, A.; Sturm, T.; Weissensteiner, W.; Martinez-Ripoll, M. Organometallics 1998, 17, 4634-4644.
11. For reviews, see: (a) Hayashi, T. In Ferrocenes; Togni, A., Hayashi, T., Eds., VCH: Weinheim, 1995; pp 105-142. (b) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377-2407. For recent examples, see: (c) Richards, C. J.; Mulvaney, A. W. Tetrahedron: Asymmetry 1996, 7, 1119-1130. (d) Nishibayashi, Y.; Segawa, K.; Arikawa, Y.; Ohe, K.; Hidai, M.; Uemura, S. J. Organomet. Chem. 1997, 546-547, 381-398. (e) Sammakia, T.; Stangeland, E. L. J. Org. Chem. 1997, 62, 6104-6105. (f) Enders, D.; Peters, R.; Lochtman, R.; Runsink, J. Synlett 1997, 1462-1464. (g) Lagneau, N. M.; Chen, Y.; Robben, P. M.; Sin, H.-S.; Takasu, K.; Chen, J.-S.; Robinson, P. D.; Hua, D. H. Tetrahedron 1997, 54, 7301-7334. (h) Chesney, A.; Bryce, M.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Synthesis 1998, 413-416. (i) Schwink, L.; Knochel, P. Chem. Eur. J. 1998, 4, 950-968. (j) Riant, O.; Argouarch, G.; Guillaneux, D.; Samuel, O.; Kagan, H. B. J. Org. Chem. 1998, 63, 3511-3514. (k) Bolm, C.; Muniz-Fernandez, K.; Seger, A.; Raabe, G.; Gunther, K. J. Org. Chem. 1998, 63, 7860-7867. (l) Torre, F. G.; Jalon, F. A.; Lopez-Agenjo, A.; Manzano, B. R.; Rodriguez, A.; Sturm, T.; Weissensteiner, W.; Martinez-Ripoll, M. Organometallics 1998, 17, 4634-4644.
12. For reviews, see: (a) Hayashi, T. In Ferrocenes; Togni, A., Hayashi, T., Eds., VCH: Weinheim, 1995; pp 105-142. (b) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377-2407. For recent examples, see: (c) Richards, C. J.; Mulvaney, A. W. Tetrahedron: Asymmetry 1996, 7, 1119-1130. (d) Nishibayashi, Y.; Segawa, K.; Arikawa, Y.; Ohe, K.; Hidai, M.; Uemura, S. J. Organomet. Chem. 1997, 546-547, 381-398. (e) Sammakia, T.; Stangeland, E. L. J. Org. Chem. 1997, 62, 6104-6105. (f) Enders, D.; Peters, R.; Lochtman, R.; Runsink, J. Synlett 1997, 1462-1464. (g) Lagneau, N. M.; Chen, Y.; Robben, P. M.; Sin, H.-S.; Takasu, K.; Chen, J.-S.; Robinson, P. D.; Hua, D. H. Tetrahedron 1997, 54, 7301-7334. (h) Chesney, A.; Bryce, M.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Synthesis 1998, 413-416. (i) Schwink, L.; Knochel, P. Chem. Eur. J. 1998, 4, 950-968. (j) Riant, O.; Argouarch, G.; Guillaneux, D.; Samuel, O.; Kagan, H. B. J. Org. Chem. 1998, 63, 3511-3514. (k) Bolm, C.; Muniz-Fernandez, K.; Seger, A.; Raabe, G.; Gunther, K. J. Org. Chem. 1998, 63, 7860-7867. (l) Torre, F. G.; Jalon, F. A.; Lopez-Agenjo, A.; Manzano, B. R.; Rodriguez, A.; Sturm, T.; Weissensteiner, W.; Martinez-Ripoll, M. Organometallics 1998, 17, 4634-4644.
13. For reviews, see: (a) Hayashi, T. In Ferrocenes; Togni, A., Hayashi, T., Eds., VCH: Weinheim, 1995; pp 105-142. (b) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377-2407. For recent examples, see: (c) Richards, C. J.; Mulvaney, A. W. Tetrahedron: Asymmetry 1996, 7, 1119-1130. (d) Nishibayashi, Y.; Segawa, K.; Arikawa, Y.; Ohe, K.; Hidai, M.; Uemura, S. J. Organomet. Chem. 1997, 546-547, 381-398. (e) Sammakia, T.; Stangeland, E. L. J. Org. Chem. 1997, 62, 6104-6105. (f) Enders, D.; Peters, R.; Lochtman, R.; Runsink, J. Synlett 1997, 1462-1464. (g) Lagneau, N. M.; Chen, Y.; Robben, P. M.; Sin, H.-S.; Takasu, K.; Chen, J.-S.; Robinson, P. D.; Hua, D. H. Tetrahedron 1997, 54, 7301-7334. (h) Chesney, A.; Bryce, M.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Synthesis 1998, 413-416. (i) Schwink, L.; Knochel, P. Chem. Eur. J. 1998, 4, 950-968. (j) Riant, O.; Argouarch, G.; Guillaneux, D.; Samuel, O.; Kagan, H. B. J. Org. Chem. 1998, 63, 3511-3514. (k) Bolm, C.; Muniz-Fernandez, K.; Seger, A.; Raabe, G.; Gunther, K. J. Org. Chem. 1998, 63, 7860-7867. (l) Torre, F. G.; Jalon, F. A.; Lopez-Agenjo, A.; Manzano, B. R.; Rodriguez, A.; Sturm, T.; Weissensteiner, W.; Martinez-Ripoll, M. Organometallics 1998, 17, 4634-4644.
14. For reviews, see: (a) Hayashi, T. In Ferrocenes; Togni, A., Hayashi, T., Eds., VCH: Weinheim, 1995; pp 105-142. (b) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377-2407. For recent examples, see: (c) Richards, C. J.; Mulvaney, A. W. Tetrahedron: Asymmetry 1996, 7, 1119-1130. (d) Nishibayashi, Y.; Segawa, K.; Arikawa, Y.; Ohe, K.; Hidai, M.; Uemura, S. J. Organomet. Chem. 1997, 546-547, 381-398. (e) Sammakia, T.; Stangeland, E. L. J. Org. Chem. 1997, 62, 6104-6105. (f) Enders, D.; Peters, R.; Lochtman, R.; Runsink, J. Synlett 1997, 1462-1464. (g) Lagneau, N. M.; Chen, Y.; Robben, P. M.; Sin, H.-S.; Takasu, K.; Chen, J.-S.; Robinson, P. D.; Hua, D. H. Tetrahedron 1997, 54, 7301-7334. (h) Chesney, A.; Bryce, M.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Synthesis 1998, 413-416. (i) Schwink, L.; Knochel, P. Chem. Eur. J. 1998, 4, 950-968. (j) Riant, O.; Argouarch, G.; Guillaneux, D.; Samuel, O.; Kagan, H. B. J. Org. Chem. 1998, 63, 3511-3514. (k) Bolm, C.; Muniz-Fernandez, K.; Seger, A.; Raabe, G.; Gunther, K. J. Org. Chem. 1998, 63, 7860-7867. (l) Torre, F. G.; Jalon, F. A.; Lopez-Agenjo, A.; Manzano, B. R.; Rodriguez, A.; Sturm, T.; Weissensteiner, W.; Martinez-Ripoll, M. Organometallics 1998, 17, 4634-4644.
15. For reviews, see: (a) Hayashi, T. In Ferrocenes; Togni, A., Hayashi, T., Eds., VCH: Weinheim, 1995; pp 105-142. (b) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377-2407. For recent examples, see: (c) Richards, C. J.; Mulvaney, A. W. Tetrahedron: Asymmetry 1996, 7, 1119-1130. (d) Nishibayashi, Y.; Segawa, K.; Arikawa, Y.; Ohe, K.; Hidai, M.; Uemura, S. J. Organomet. Chem. 1997, 546-547, 381-398. (e) Sammakia, T.; Stangeland, E. L. J. Org. Chem. 1997, 62, 6104-6105. (f) Enders, D.; Peters, R.; Lochtman, R.; Runsink, J. Synlett 1997, 1462-1464. (g) Lagneau, N. M.; Chen, Y.; Robben, P. M.; Sin, H.-S.; Takasu, K.; Chen, J.-S.; Robinson, P. D.; Hua, D. H. Tetrahedron 1997, 54, 7301-7334. (h) Chesney, A.; Bryce, M.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Synthesis 1998, 413-416. (i) Schwink, L.; Knochel, P. Chem. Eur. J. 1998, 4, 950-968. (j) Riant, O.; Argouarch, G.; Guillaneux, D.; Samuel, O.; Kagan, H. B. J. Org. Chem. 1998, 63, 3511-3514. (k) Bolm, C.; Muniz-Fernandez, K.; Seger, A.; Raabe, G.; Gunther, K. J. Org. Chem. 1998, 63, 7860-7867. (l) Torre, F. G.; Jalon, F. A.; Lopez-Agenjo, A.; Manzano, B. R.; Rodriguez, A.; Sturm, T.; Weissensteiner, W.; Martinez-Ripoll, M. Organometallics 1998, 17, 4634-4644.
16. For reviews, see: (a) Hayashi, T. In Ferrocenes; Togni, A., Hayashi, T., Eds., VCH: Weinheim, 1995; pp 105-142. (b) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377-2407. For recent examples, see: (c) Richards, C. J.; Mulvaney, A. W. Tetrahedron: Asymmetry 1996, 7, 1119-1130. (d) Nishibayashi, Y.; Segawa, K.; Arikawa, Y.; Ohe, K.; Hidai, M.; Uemura, S. J. Organomet. Chem. 1997, 546-547, 381-398. (e) Sammakia, T.; Stangeland, E. L. J. Org. Chem. 1997, 62, 6104-6105. (f) Enders, D.; Peters, R.; Lochtman, R.; Runsink, J. Synlett 1997, 1462-1464. (g) Lagneau, N. M.; Chen, Y.; Robben, P. M.; Sin, H.-S.; Takasu, K.; Chen, J.-S.; Robinson, P. D.; Hua, D. H. Tetrahedron 1997, 54, 7301-7334. (h) Chesney, A.; Bryce, M.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Synthesis 1998, 413-416. (i) Schwink, L.; Knochel, P. Chem. Eur. J. 1998, 4, 950-968. (j) Riant, O.; Argouarch, G.; Guillaneux, D.; Samuel, O.; Kagan, H. B. J. Org. Chem. 1998, 63, 3511-3514. (k) Bolm, C.; Muniz-Fernandez, K.; Seger, A.; Raabe, G.; Gunther, K. J. Org. Chem. 1998, 63, 7860-7867. (l) Torre, F. G.; Jalon, F. A.; Lopez-Agenjo, A.; Manzano, B. R.; Rodriguez, A.; Sturm, T.; Weissensteiner, W.; Martinez-Ripoll, M. Organometallics 1998, 17, 4634-4644.
17. For reviews, see: (a) Hayashi, T. In Ferrocenes; Togni, A., Hayashi, T., Eds., VCH: Weinheim, 1995; pp 105-142. (b) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377-2407. For recent examples, see: (c) Richards, C. J.; Mulvaney, A. W. Tetrahedron: Asymmetry 1996, 7, 1119-1130. (d) Nishibayashi, Y.; Segawa, K.; Arikawa, Y.; Ohe, K.; Hidai, M.; Uemura, S. J. Organomet. Chem. 1997, 546-547, 381-398. (e) Sammakia, T.; Stangeland, E. L. J. Org. Chem. 1997, 62, 6104-6105. (f) Enders, D.; Peters, R.; Lochtman, R.; Runsink, J. Synlett 1997, 1462-1464. (g) Lagneau, N. M.; Chen, Y.; Robben, P. M.; Sin, H.-S.; Takasu, K.; Chen, J.-S.; Robinson, P. D.; Hua, D. H. Tetrahedron 1997, 54, 7301-7334. (h) Chesney, A.; Bryce, M.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Synthesis 1998, 413-416. (i) Schwink, L.; Knochel, P. Chem. Eur. J. 1998, 4, 950-968. (j) Riant, O.; Argouarch, G.; Guillaneux, D.; Samuel, O.; Kagan, H. B. J. Org. Chem. 1998, 63, 3511-3514. (k) Bolm, C.; Muniz-Fernandez, K.; Seger, A.; Raabe, G.; Gunther, K. J. Org. Chem. 1998, 63, 7860-7867. (l) Torre, F. G.; Jalon, F. A.; Lopez-Agenjo, A.; Manzano, B. R.; Rodriguez, A.; Sturm, T.; Weissensteiner, W.; Martinez-Ripoll, M. Organometallics 1998, 17, 4634-4644.
18. For reviews, see: (a) Hayashi, T. In Ferrocenes; Togni, A., Hayashi, T., Eds., VCH: Weinheim, 1995; pp 105-142. (b) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377-2407. For recent examples, see: (c) Richards, C. J.; Mulvaney, A. W. Tetrahedron: Asymmetry 1996, 7, 1119-1130. (d) Nishibayashi, Y.; Segawa, K.; Arikawa, Y.; Ohe, K.; Hidai, M.; Uemura, S. J. Organomet. Chem. 1997, 546-547, 381-398. (e) Sammakia, T.; Stangeland, E. L. J. Org. Chem. 1997, 62, 6104-6105. (f) Enders, D.; Peters, R.; Lochtman, R.; Runsink, J. Synlett 1997, 1462-1464. (g) Lagneau, N. M.; Chen, Y.; Robben, P. M.; Sin, H.-S.; Takasu, K.; Chen, J.-S.; Robinson, P. D.; Hua, D. H. Tetrahedron 1997, 54, 7301-7334. (h) Chesney, A.; Bryce, M.; Chubb, R. W. J.; Batsanov, A. S.; Howard, J. A. K. Synthesis 1998, 413-416. (i) Schwink, L.; Knochel, P. Chem. Eur. J. 1998, 4, 950-968. (j) Riant, O.; Argouarch, G.; Guillaneux, D.; Samuel, O.; Kagan, H. B. J. Org. Chem. 1998, 63, 3511-3514. (k) Bolm, C.; Muniz-Fernandez, K.; Seger, A.; Raabe, G.; Gunther, K. J. Org. Chem. 1998, 63, 7860-7867. (l) Torre, F. G.; Jalon, F. A.; Lopez-Agenjo, A.; Manzano, B. R.; Rodriguez, A.; Sturm, T.; Weissensteiner, W.; Martinez-Ripoll, M. Organometallics 1998, 17, 4634-4644.
19. (a) Hayashi, T.; Yamamoto, A.; Hojo, M.; Ito, Y. J. Chem. Soc., Chem. Commun. 1989, 495-496.
20. (b) Hayashi, T.; Yamamoto, A.; Hojo, M.; Kishi, K.; Ito, Y.; Nishioka, E.; Miura, H.; Yanagi, K. J. Organomet. Chem. 1989, 370, 129-139.
21. (c) Park, J.; Lee, S.; Ahn, K. H.; Cho, C.-H. Tetrahedron Lett. 1995, 36, 7263-7267.
22. (d) Schwink, L.; Knochel, P. Tetrahedron Lett. 1996, 37, 25-28.
23. (e) Park, J.; Lee, S.; Ahn, K. H.; Cho, C.-H. Tetrahedron Lett. 1996, 37, 6137-6140.
24. (f) Enders, D.; Lochtman, R. Synlett 1997, 355-356.
25. (g) Ahn, K. H.; Cho, C.-H.; Park, J.; Lee, S. Tetrahedron: Asymmetry 1997, 8, 1179-1185.
26. (h) Perea, J. J. A.; Borner, A.; Knochel, P. Tetrahedron Lett. 1998, 39, 8073-8076.
27. (a) Zhang, W.; Adachi, Y.; Hirao, T.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 451-460.
28. (b) Zhang, W.; Hirao, T.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545-4548.
29. 2-symmetric ferrocene derivatives with only the planar chirality appeared: (a) Jendralla, H.; Paulus, E. Synlett 1997, 471-472. (b) Kang J.; Lee, J. H.; Ahn, S. H.; Choi, J. S. Tetrahedron Lett. 1998, 39, 5523-5526. (c) Iftime, G.; Daran, J.-C.; Manoury, E.; Balavoine, G. G. A. Angew. Chem., Int. Ed. Engl. 1998, 37, 1698-1701. (d) Iftime, G.; Daran, J.-C.; Manoury, E.; Balavoine, G. G. A. J. Organomet. Chem. 1998, 565, 115-124. (e) Zhang, W.; Yoneda, Y.; Kida, T.; Nakatsuji, Y.; Ikeda, I. J. Organomet. Chem. 1999, 574(1), 19-23.
30. 2-symmetric ferrocene derivatives with only the planar chirality appeared: (a) Jendralla, H.; Paulus, E. Synlett 1997, 471-472. (b) Kang J.; Lee, J. H.; Ahn, S. H.; Choi, J. S. Tetrahedron Lett. 1998, 39, 5523-5526. (c) Iftime, G.; Daran, J.-C.; Manoury, E.; Balavoine, G. G. A. Angew. Chem., Int. Ed. Engl. 1998, 37, 1698-1701. (d) Iftime, G.; Daran, J.-C.; Manoury, E.; Balavoine, G. G. A. J. Organomet. Chem. 1998, 565, 115-124. (e) Zhang, W.; Yoneda, Y.; Kida, T.; Nakatsuji, Y.; Ikeda, I. J. Organomet. Chem. 1999, 574(1), 19-23.
31. 2-symmetric ferrocene derivatives with only the planar chirality appeared: (a) Jendralla, H.; Paulus, E. Synlett 1997, 471-472. (b) Kang J.; Lee, J. H.; Ahn, S. H.; Choi, J. S. Tetrahedron Lett. 1998, 39, 5523-5526. (c) Iftime, G.; Daran, J.-C.; Manoury, E.; Balavoine, G. G. A. Angew. Chem., Int. Ed. Engl. 1998, 37, 1698-1701. (d) Iftime, G.; Daran, J.-C.; Manoury, E.; Balavoine, G. G. A. J. Organomet. Chem. 1998, 565, 115-124. (e) Zhang, W.; Yoneda, Y.; Kida, T.; Nakatsuji, Y.; Ikeda, I. J. Organomet. Chem. 1999, 574(1), 19-23.
32. 2-symmetric ferrocene derivatives with only the planar chirality appeared: (a) Jendralla, H.; Paulus, E. Synlett 1997, 471-472. (b) Kang J.; Lee, J. H.; Ahn, S. H.; Choi, J. S. Tetrahedron Lett. 1998, 39, 5523-5526. (c) Iftime, G.; Daran, J.-C.; Manoury, E.; Balavoine, G. G. A. Angew. Chem., Int. Ed. Engl. 1998, 37, 1698-1701. (d) Iftime, G.; Daran, J.-C.; Manoury, E.; Balavoine, G. G. A. J. Organomet. Chem. 1998, 565, 115-124. (e) Zhang, W.; Yoneda, Y.; Kida, T.; Nakatsuji, Y.; Ikeda, I. J. Organomet. Chem. 1999, 574(1), 19-23.
33. 2-symmetric ferrocene derivatives with only the planar chirality appeared: (a) Jendralla, H.; Paulus, E. Synlett 1997, 471-472. (b) Kang J.; Lee, J. H.; Ahn, S. H.; Choi, J. S. Tetrahedron Lett. 1998, 39, 5523-5526. (c) Iftime, G.; Daran, J.-C.; Manoury, E.; Balavoine, G. G. A. Angew. Chem., Int. Ed. Engl. 1998, 37, 1698-1701. (d) Iftime, G.; Daran, J.-C.; Manoury, E.; Balavoine, G. G. A. J. Organomet. Chem. 1998, 565, 115-124. (e) Zhang, W.; Yoneda, Y.; Kida, T.; Nakatsuji, Y.; Ikeda, I. J. Organomet. Chem. 1999, 574(1), 19-23.
34. (a) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 2453-2462.
35. (b) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1997, 38, 2681-2684.
36. (c) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1998, 39, 4343-4346.
37. (d) Zhang, W.; Yoneda, Y.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron: Asymmetry 1998, 9, 3371-3380.
38. (e) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Chem. Lett. 1999, 243-244.
39. (f) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Synlett 1999, 1319-1321.
40. 2-symmetric ferrocene liganda with only planar chirality, a part of this work has been communicated; see: Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1996, 37, 7995-7998.
41. For reviews, see: (a) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089-1122. (b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 325-365. (c) Reiser, O. Angew. Chem., Int. Ed. Engl. 1993, 32, 547- 549. (d) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395- 422. (e) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45.
42. For reviews, see: (a) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089-1122. (b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 325-365. (c) Reiser, O. Angew. Chem., Int. Ed. Engl. 1993, 32, 547- 549. (d) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395- 422. (e) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45.
43. For reviews, see: (a) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089-1122. (b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 325-365. (c) Reiser, O. Angew. Chem., Int. Ed. Engl. 1993, 32, 547-549. (d) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395- 422. (e) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45.
44. For reviews, see: (a) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089-1122. (b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 325-365. (c) Reiser, O. Angew. Chem., Int. Ed. Engl. 1993, 32, 547- 549. (d) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422. (e) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45.
45. For reviews, see: (a) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089-1122. (b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 325-365. (c) Reiser, O. Angew. Chem., Int. Ed. Engl. 1993, 32, 547- 549. (d) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395- 422. (e) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1-45.
46. Selected papers for N,N-chelating ligands: (a) Pfaltz, P. Acc. Chem. Res. 1993, 26, 339-345. (b) Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135-8138. (c) Kang, J.; Cho, W. O.; Cho, H. G. Tetrahedron: Asymmetry 1994, 5, 1347-1352. (d) Hoarao, O.; Ait-Haddou, H.; Castro, M.; Balavoine, G. G. A. Tetrahedron: Asymmetry 1997, 8, 3755-3764. (e) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437-3443. Selected papers for P,N-chelating ligands: (f) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769-1772. (g) Matt, P.-V.; Pfalts, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568. (h) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149-3150. (i) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493-4506. (j) Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689-6692. (k) Wimmer, P.; Widhalm, M. Tetrahedron: Asymmetry 1995, 6, 657-660. (l) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031-1037. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583-584. (n) Cahill, J. P.; Guiry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301-4305. (o) Vyskocil, S.; Smrcina, M.; Hanus, V.; Polasek, M.; Kocovsky, P. J. Org. Chem. 1998, 63, 7738- 7748. (p) Gilbertson, S. R.; Chang, C.-W. T. J. Org. Chem. 1998, 63, 8424-8431.
47. Selected papers for N,N-chelating ligands: (a) Pfaltz, P. Acc. Chem. Res. 1993, 26, 339-345. (b) Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135-8138. (c) Kang, J.; Cho, W. O.; Cho, H. G. Tetrahedron: Asymmetry 1994, 5, 1347-1352. (d) Hoarao, O.; Ait-Haddou, H.; Castro, M.; Balavoine, G. G. A. Tetrahedron: Asymmetry 1997, 8, 3755-3764. (e) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437-3443. Selected papers for P,N-chelating ligands: (f) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769-1772. (g) Matt, P.-V.; Pfalts, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568. (h) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149-3150. (i) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493-4506. (j) Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689-6692. (k) Wimmer, P.; Widhalm, M. Tetrahedron: Asymmetry 1995, 6, 657-660. (l) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031-1037. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583-584. (n) Cahill, J. P.; Guiry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301-4305. (o) Vyskocil, S.; Smrcina, M.; Hanus, V.; Polasek, M.; Kocovsky, P. J. Org. Chem. 1998, 63, 7738- 7748. (p) Gilbertson, S. R.; Chang, C.-W. T. J. Org. Chem. 1998, 63, 8424-8431.
48. Selected papers for N,N-chelating ligands: (a) Pfaltz, P. Acc. Chem. Res. 1993, 26, 339-345. (b) Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135-8138. (c) Kang, J.; Cho, W. O.; Cho, H. G. Tetrahedron: Asymmetry 1994, 5, 1347-1352. (d) Hoarao, O.; Ait-Haddou, H.; Castro, M.; Balavoine, G. G. A. Tetrahedron: Asymmetry 1997, 8, 3755-3764. (e) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437-3443. Selected papers for P,N-chelating ligands: (f) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769-1772. (g) Matt, P.-V.; Pfalts, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568. (h) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149-3150. (i) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493-4506. (j) Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689-6692. (k) Wimmer, P.; Widhalm, M. Tetrahedron: Asymmetry 1995, 6, 657-660. (l) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031-1037. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583-584. (n) Cahill, J. P.; Guiry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301-4305. (o) Vyskocil, S.; Smrcina, M.; Hanus, V.; Polasek, M.; Kocovsky, P. J. Org. Chem. 1998, 63, 7738- 7748. (p) Gilbertson, S. R.; Chang, C.-W. T. J. Org. Chem. 1998, 63, 8424-8431.
49. Selected papers for N,N-chelating ligands: (a) Pfaltz, P. Acc. Chem. Res. 1993, 26, 339-345. (b) Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135-8138. (c) Kang, J.; Cho, W. O.; Cho, H. G. Tetrahedron: Asymmetry 1994, 5, 1347-1352. (d) Hoarao, O.; Ait-Haddou, H.; Castro, M.; Balavoine, G. G. A. Tetrahedron: Asymmetry 1997, 8, 3755-3764. (e) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437-3443. Selected papers for P,N-chelating ligands: (f) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769-1772. (g) Matt, P.-V.; Pfalts, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568. (h) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149-3150. (i) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493-4506. (j) Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689-6692. (k) Wimmer, P.; Widhalm, M. Tetrahedron: Asymmetry 1995, 6, 657-660. (l) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031-1037. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583-584. (n) Cahill, J. P.; Guiry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301-4305. (o) Vyskocil, S.; Smrcina, M.; Hanus, V.; Polasek, M.; Kocovsky, P. J. Org. Chem. 1998, 63, 7738- 7748. (p) Gilbertson, S. R.; Chang, C.-W. T. J. Org. Chem. 1998, 63, 8424-8431.
50. Selected papers for N,N-chelating ligands: (a) Pfaltz, P. Acc. Chem. Res. 1993, 26, 339-345. (b) Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135-8138. (c) Kang, J.; Cho, W. O.; Cho, H. G. Tetrahedron: Asymmetry 1994, 5, 1347-1352. (d) Hoarao, O.; Ait-Haddou, H.; Castro, M.; Balavoine, G. G. A. Tetrahedron: Asymmetry 1997, 8, 3755-3764. (e) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437-3443. Selected papers for P,N-chelating ligands: (f) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769-1772. (g) Matt, P.-V.; Pfalts, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568. (h) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149-3150. (i) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493-4506. (j) Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689-6692. (k) Wimmer, P.; Widhalm, M. Tetrahedron: Asymmetry 1995, 6, 657-660. (l) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031-1037. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583-584. (n) Cahill, J. P.; Guiry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301-4305. (o) Vyskocil, S.; Smrcina, M.; Hanus, V.; Polasek, M.; Kocovsky, P. J. Org. Chem. 1998, 63, 7738- 7748. (p) Gilbertson, S. R.; Chang, C.-W. T. J. Org. Chem. 1998, 63, 8424-8431.
51. Selected papers for N,N-chelating ligands: (a) Pfaltz, P. Acc. Chem. Res. 1993, 26, 339-345. (b) Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135-8138. (c) Kang, J.; Cho, W. O.; Cho, H. G. Tetrahedron: Asymmetry 1994, 5, 1347-1352. (d) Hoarao, O.; Ait-Haddou, H.; Castro, M.; Balavoine, G. G. A. Tetrahedron: Asymmetry 1997, 8, 3755-3764. (e) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437-3443. Selected papers for P,N-chelating ligands: (f) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769-1772. (g) Matt, P.-V.; Pfalts, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568. (h) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149-3150. (i) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493-4506. (j) Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689-6692. (k) Wimmer, P.; Widhalm, M. Tetrahedron: Asymmetry 1995, 6, 657-660. (l) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031-1037. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583-584. (n) Cahill, J. P.; Guiry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301-4305. (o) Vyskocil, S.; Smrcina, M.; Hanus, V.; Polasek, M.; Kocovsky, P. J. Org. Chem. 1998, 63, 7738- 7748. (p) Gilbertson, S. R.; Chang, C.-W. T. J. Org. Chem. 1998, 63, 8424-8431.
52. Selected papers for N,N-chelating ligands: (a) Pfaltz, P. Acc. Chem. Res. 1993, 26, 339-345. (b) Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135-8138. (c) Kang, J.; Cho, W. O.; Cho, H. G. Tetrahedron: Asymmetry 1994, 5, 1347-1352. (d) Hoarao, O.; Ait-Haddou, H.; Castro, M.; Balavoine, G. G. A. Tetrahedron: Asymmetry 1997, 8, 3755-3764. (e) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437-3443. Selected papers for P,N-chelating ligands: (f) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769-1772. (g) Matt, P.-V.; Pfalts, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568. (h) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149-3150. (i) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493-4506. (j) Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689-6692. (k) Wimmer, P.; Widhalm, M. Tetrahedron: Asymmetry 1995, 6, 657-660. (l) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031-1037. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583-584. (n) Cahill, J. P.; Guiry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301-4305. (o) Vyskocil, S.; Smrcina, M.; Hanus, V.; Polasek, M.; Kocovsky, P. J. Org. Chem. 1998, 63, 7738- 7748. (p) Gilbertson, S. R.; Chang, C.-W. T. J. Org. Chem. 1998, 63, 8424-8431.
53. Selected papers for N,N-chelating ligands: (a) Pfaltz, P. Acc. Chem. Res. 1993, 26, 339-345. (b) Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135-8138. (c) Kang, J.; Cho, W. O.; Cho, H. G. Tetrahedron: Asymmetry 1994, 5, 1347-1352. (d) Hoarao, O.; Ait-Haddou, H.; Castro, M.; Balavoine, G. G. A. Tetrahedron: Asymmetry 1997, 8, 3755-3764. (e) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437-3443. Selected papers for P,N-chelating ligands: (f) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769-1772. (g) Matt, P.-V.; Pfalts, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568. (h) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149-3150. (i) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493-4506. (j) Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689-6692. (k) Wimmer, P.; Widhalm, M. Tetrahedron: Asymmetry 1995, 6, 657-660. (l) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031-1037. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583-584. (n) Cahill, J. P.; Guiry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301-4305. (o) Vyskocil, S.; Smrcina, M.; Hanus, V.; Polasek, M.; Kocovsky, P. J. Org. Chem. 1998, 63, 7738- 7748. (p) Gilbertson, S. R.; Chang, C.-W. T. J. Org. Chem. 1998, 63, 8424-8431.
54. Selected papers for N,N-chelating ligands: (a) Pfaltz, P. Acc. Chem. Res. 1993, 26, 339-345. (b) Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135-8138. (c) Kang, J.; Cho, W. O.; Cho, H. G. Tetrahedron: Asymmetry 1994, 5, 1347-1352. (d) Hoarao, O.; Ait-Haddou, H.; Castro, M.; Balavoine, G. G. A. Tetrahedron: Asymmetry 1997, 8, 3755-3764. (e) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437-3443. Selected papers for P,N-chelating ligands: (f) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769-1772. (g) Matt, P.-V.; Pfalts, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568. (h) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149-3150. (i) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493-4506. (j) Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689-6692. (k) Wimmer, P.; Widhalm, M. Tetrahedron: Asymmetry 1995, 6, 657-660. (l) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031-1037. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583-584. (n) Cahill, J. P.; Guiry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301-4305. (o) Vyskocil, S.; Smrcina, M.; Hanus, V.; Polasek, M.; Kocovsky, P. J. Org. Chem. 1998, 63, 7738- 7748. (p) Gilbertson, S. R.; Chang, C.-W. T. J. Org. Chem. 1998, 63, 8424-8431.
55. Selected papers for N,N-chelating ligands: (a) Pfaltz, P. Acc. Chem. Res. 1993, 26, 339-345. (b) Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135-8138. (c) Kang, J.; Cho, W. O.; Cho, H. G. Tetrahedron: Asymmetry 1994, 5, 1347-1352. (d) Hoarao, O.; Ait-Haddou, H.; Castro, M.; Balavoine, G. G. A. Tetrahedron: Asymmetry 1997, 8, 3755-3764. (e) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437-3443. Selected papers for P,N-chelating ligands: (f) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769-1772. (g) Matt, P.-V.; Pfalts, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568. (h) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149-3150. (i) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493-4506. (j) Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689-6692. (k) Wimmer, P.; Widhalm, M. Tetrahedron: Asymmetry 1995, 6, 657-660. (l) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031-1037. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583-584. (n) Cahill, J. P.; Guiry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301-4305. (o) Vyskocil, S.; Smrcina, M.; Hanus, V.; Polasek, M.; Kocovsky, P. J. Org. Chem. 1998, 63, 7738- 7748. (p) Gilbertson, S. R.; Chang, C.-W. T. J. Org. Chem. 1998, 63, 8424-8431.
56. Selected papers for N,N-chelating ligands: (a) Pfaltz, P. Acc. Chem. Res. 1993, 26, 339-345. (b) Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135-8138. (c) Kang, J.; Cho, W. O.; Cho, H. G. Tetrahedron: Asymmetry 1994, 5, 1347-1352. (d) Hoarao, O.; Ait-Haddou, H.; Castro, M.; Balavoine, G. G. A. Tetrahedron: Asymmetry 1997, 8, 3755-3764. (e) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437-3443. Selected papers for P,N-chelating ligands: (f) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769-1772. (g) Matt, P.-V.; Pfalts, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568. (h) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149-3150. (i) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493-4506. (j) Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689-6692. (k) Wimmer, P.; Widhalm, M. Tetrahedron: Asymmetry 1995, 6, 657-660. (l) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031-1037. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583-584. (n) Cahill, J. P.; Guiry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301-4305. (o) Vyskocil, S.; Smrcina, M.; Hanus, V.; Polasek, M.; Kocovsky, P. J. Org. Chem. 1998, 63, 7738- 7748. (p) Gilbertson, S. R.; Chang, C.-W. T. J. Org. Chem. 1998, 63, 8424-8431.
57. Selected papers for N,N-chelating ligands: (a) Pfaltz, P. Acc. Chem. Res. 1993, 26, 339-345. (b) Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135-8138. (c) Kang, J.; Cho, W. O.; Cho, H. G. Tetrahedron: Asymmetry 1994, 5, 1347-1352. (d) Hoarao, O.; Ait-Haddou, H.; Castro, M.; Balavoine, G. G. A. Tetrahedron: Asymmetry 1997, 8, 3755-3764. (e) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437-3443. Selected papers for P,N-chelating ligands: (f) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769-1772. (g) Matt, P.-V.; Pfalts, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568. (h) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149-3150. (i) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493-4506. (j) Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689-6692. (k) Wimmer, P.; Widhalm, M. Tetrahedron: Asymmetry 1995, 6, 657-660. (l) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031-1037. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583-584. (n) Cahill, J. P.; Guiry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301-4305. (o) Vyskocil, S.; Smrcina, M.; Hanus, V.; Polasek, M.; Kocovsky, P. J. Org. Chem. 1998, 63, 7738- 7748. (p) Gilbertson, S. R.; Chang, C.-W. T. J. Org. Chem. 1998, 63, 8424-8431.
58. Selected papers for N,N-chelating ligands: (a) Pfaltz, P. Acc. Chem. Res. 1993, 26, 339-345. (b) Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135-8138. (c) Kang, J.; Cho, W. O.; Cho, H. G. Tetrahedron: Asymmetry 1994, 5, 1347-1352. (d) Hoarao, O.; Ait-Haddou, H.; Castro, M.; Balavoine, G. G. A. Tetrahedron: Asymmetry 1997, 8, 3755-3764. (e) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437-3443. Selected papers for P,N-chelating ligands: (f) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769-1772. (g) Matt, P.-V.; Pfalts, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568. (h) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149-3150. (i) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493-4506. (j) Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689-6692. (k) Wimmer, P.; Widhalm, M. Tetrahedron: Asymmetry 1995, 6, 657-660. (l) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031-1037. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583-584. (n) Cahill, J. P.; Guiry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301-4305. (o) Vyskocil, S.; Smrcina, M.; Hanus, V.; Polasek, M.; Kocovsky, P. J. Org. Chem. 1998, 63, 7738- 7748. (p) Gilbertson, S. R.; Chang, C.-W. T. J. Org. Chem. 1998, 63, 8424-8431.
59. Selected papers for N,N-chelating ligands: (a) Pfaltz, P. Acc. Chem. Res. 1993, 26, 339-345. (b) Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135-8138. (c) Kang, J.; Cho, W. O.; Cho, H. G. Tetrahedron: Asymmetry 1994, 5, 1347-1352. (d) Hoarao, O.; Ait-Haddou, H.; Castro, M.; Balavoine, G. G. A. Tetrahedron: Asymmetry 1997, 8, 3755-3764. (e) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437-3443. Selected papers for P,N-chelating ligands: (f) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769-1772. (g) Matt, P.-V.; Pfalts, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568. (h) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149-3150. (i) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493-4506. (j) Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689-6692. (k) Wimmer, P.; Widhalm, M. Tetrahedron: Asymmetry 1995, 6, 657-660. (l) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031-1037. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583-584. (n) Cahill, J. P.; Guiry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301-4305. (o) Vyskocil, S.; Smrcina, M.; Hanus, V.; Polasek, M.; Kocovsky, P. J. Org. Chem. 1998, 63, 7738- 7748. (p) Gilbertson, S. R.; Chang, C.-W. T. J. Org. Chem. 1998, 63, 8424-8431.
60. Selected papers for N,N-chelating ligands: (a) Pfaltz, P. Acc. Chem. Res. 1993, 26, 339-345. (b) Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135-8138. (c) Kang, J.; Cho, W. O.; Cho, H. G. Tetrahedron: Asymmetry 1994, 5, 1347-1352. (d) Hoarao, O.; Ait-Haddou, H.; Castro, M.; Balavoine, G. G. A. Tetrahedron: Asymmetry 1997, 8, 3755-3764. (e) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437-3443. Selected papers for P,N-chelating ligands: (f) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769-1772. (g) Matt, P.-V.; Pfalts, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568. (h) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149-3150. (i) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493-4506. (j) Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689-6692. (k) Wimmer, P.; Widhalm, M. Tetrahedron: Asymmetry 1995, 6, 657-660. (l) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031-1037. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583-584. (n) Cahill, J. P.; Guiry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301-4305. (o) Vyskocil, S.; Smrcina, M.; Hanus, V.; Polasek, M.; Kocovsky, P. J. Org. Chem. 1998, 63, 7738-7748. (p) Gilbertson, S. R.; Chang, C.-W. T. J. Org. Chem. 1998, 63, 8424-8431.
61. Selected papers for N,N-chelating ligands: (a) Pfaltz, P. Acc. Chem. Res. 1993, 26, 339-345. (b) Kubota, H.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1993, 34, 8135-8138. (c) Kang, J.; Cho, W. O.; Cho, H. G. Tetrahedron: Asymmetry 1994, 5, 1347-1352. (d) Hoarao, O.; Ait-Haddou, H.; Castro, M.; Balavoine, G. G. A. Tetrahedron: Asymmetry 1997, 8, 3755-3764. (e) Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437-3443. Selected papers for P,N-chelating ligands: (f) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769-1772. (g) Matt, P.-V.; Pfalts, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568. (h) Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149-3150. (i) Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493-4506. (j) Kubota, H.; Koga, K. Tetrahedron Lett. 1994, 35, 6689-6692. (k) Wimmer, P.; Widhalm, M. Tetrahedron: Asymmetry 1995, 6, 657-660. (l) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P. S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031-1037. (m) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583-584. (n) Cahill, J. P.; Guiry, P. J. Tetrahedron: Asymmetry 1998, 9, 4301-4305. (o) Vyskocil, S.; Smrcina, M.; Hanus, V.; Polasek, M.; Kocovsky, P. J. Org. Chem. 1998, 63, 7738- 7748. (p) Gilbertson, S. R.; Chang, C.-W. T. J. Org. Chem. 1998, 63, 8424-8431.
62. (a) Hayashi, T.; Yamamoto, A.; Hagihara, T.; Ito, Y. Tetrahedron Lett. 1986, 27, 191-194.
63. (b) Yamaguchi, M.; Shima, T.; Yamagishi, T.; Hida, M. Tetrahedron: Asymmetry 1991, 2, 663-666.
64. (c) Pregosin, P. S.; Ruegger, H.; Salzmann, R.; Albinati, A.; Lianza, F.; Kunz, R. W. Organometallics 1994, 13, 83-90.
65. (d) Dierkes, P.; Ramdeehul, S.; Barloy, L.; Cian, A. D.; Fischer, J.; Kamer, P. C. J.; Leeuwen, P. W. N. M.; Osborn, J. A. Angew. Chem., Int. Ed. Engl. 1998, 37, 3116-3118.
66. (a) Allen, J. V.; Coote, S. J.; Dawson, G. J.; Frost, C. G.; Martin, C. J.; William, J. M. J. J. Chem. Soc., Perkin Trans, 1 1994, 2065-2072.
67. (b) Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem., Int. Ed. Engl. 1993, 34, 2386-2388. Also see refs 3g, 9c, 9g, 9o, and 10d.
68. (a) Togni, A. Tetrahedron: Asymmetry 1991, 2, 683-690.
69. (b) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089-4090.
70. (c) Sennhenn, P.; Gabler, B.; Helmchen, G. Tetrahedron Lett. 1994, 35, 8595-8598.
71. (d) Knuhl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845-1846.
72. (e) Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1998, 37, 3047-3050. Also see refs 9c, 9i, and 10d.
73. (a) Warshawsky, A. M.; Meyer, A. I. J. Am. Chem. Soc. 1990, 112, 8090-8099.
74. (b) Nelson, T. D.; Meyer, A. I. J. Org. Chem. 1994, 59, 2655-2658.
75. For a review, see: Holz, J.; Quirmbach, M.; Borner, A. Synthesis 1997, 983-1006.