Enantioselective Addition of Dialkylzincs to Aldehydes Promoted by Chiral Amino Alcohols. Mechanism and Nonlinear Effect

Journal of the American Chemical Society

Volumn 111, Issue 11, 1989, Pages 4028-4036

  Kitamura, M ^a   Okada, S ^a   Suga, S ^a   Noyori, R ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0040514974     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00193a040     Document Type: Article

References (10)

1. Boersma, J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed.; Pergamon Press: New York, 1982; Chapter 16.
2. Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071.
3. For related reactions, see: (a) Oguni, N.; Omi, T. Tetrahedron Lett. 1984, 25, 2823. (b) Smaardijk, A. A.; Wynberg, H. J. Org. Chem. 1987, 52, 135. (c) Itsuno, S.; Frechet, J. M. J. J. Org. Chem. 1987, 52, 4140. (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, T. J. Chem. Soc., Chem. Commun. 1987 467. Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111. (e) Chaloner, P. A.; Perera, S. A. R. Tetrahedron Lett. 1987, 28, 3013. (f) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233. (g) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5237. (h) Evans, D. A. Science 1988, 240, 420.
4. Coates, G. E.; Ridley, D. J. Chem. Soc. A 1966, 1064. (b) Boersma, J.; Noltes, J. G. J. Organomet. Chem. 1968, 13, 291.
5. Reetz, M. T.; Hüllmann, M.; Massa, W.; Berger, S.; Rademacher, P.; Heymanns, P. J. Am. Chem. Soc. 1986, 108, 2405.
6. Kaufmann, E.; Schleyer P. v. R.; Houk, K. N.; Wu, Y.-D. J. Am. Chem. Soc. 1985, 107, 5560.
7. Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353. For enantiomeric recognition and interactions in stoichiometric reactions, see: Wynberg, H.; Feringa, B. Tetrahedron 1976, 32, 2831.
8. Agami, C.; Puchot, C. J. Mol. Catal. 1986, 38, 341. Agami, C. Bull. Soc. Chim. Fr. 1988, 499.
9. Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M. Pure Appl. Chem. 1988, 60, 1597. (b) Oguni, N.; Matsuda, Y.; Kaneko, T. J. Am. Chem. Soc. 1988, 110, 7877.
10. Beckett, A. H.; Lan, N. T.; McDonough, G. R. Tetrahedron 1969, 25, 5689. (b) Chittenden, R. A.; Cooper, G. H. J. Chem. Soc. C 1970, 49. (c) Pauling, H. Helv. Chim. Acta 1975, 58, 1781.