Conclusions
A quadrant rule is proposed for the enantioselective reduction of acetophenone by chiral hydrides based on LiAlH4, NaBH4, LiBH4, and BH3. This enables the configuration of the product to be explained and predicted, depending on the preferred conformations of the ligands in these hydrides.
Similar content being viewed by others
Literature cited
H. Suda, S. Kanon, and N. Umeda, Chem. Lett., 899 (1984).
R. Noyori, I. Tomino, and Y. Tanimoto, J. Am. Chem. Soc.,101, 3129 (1979).
J. M. Hawkins and K. B. Sharpless, J. Org. Chem.,49, 3861 (1984).
M. Asami, H. Ohno, S. Kobayashi, and T. Mukaiyama, Bull. Chem. Soc., Jpn.,51, 1869 (1978).
J. D. Morrison, E. R. Grandbois, S. I. Howard, and G. R. Weisman, Tetrahedron Lett.,22, 2619 (1981).
K. Soai, T. Yamanoi, and H. Oyamada, Chem. Lett., 251 (1984).
K. Soai, H. Oyamada, and T. Yamanoi, J. Chem. Soc., Chem. Commun., 413 (1984) (Corrigendum, J. Chem. Soc. Chem. Commun., 308 (1985)).
A. Hirao, S. Itsuno, M. Owa, S. Nagai, H. Mochizuki, and H. H. Zoorov, J. Chem. Soc., Perkin Trans. 1, 900 (1981).
S. Itsuno, K. Ito, A. Hirao, and S. Nakahama, J. Chem. Soc., Chem. Commun., 469 (1983).
S. Itsuno, A. Hirao, S. Nakahama, and N. Yamazaki, J. Chem. Soc., Perkin Trans. 1, 1673 (1983).
Yu. T. Struchkov, A. I. Yanovskii, V. A. Pavlov, A. A. Voloboev, and E. I. Klabunovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 518 (1987).
R. J. Abraham, L. D. Hall, L. Hough, and K. A. McLauchlan, J. Chem. Soc., 3699 (1962).
R. L. Whistler and M. L. Wolform (eds.), Methods in Carbohydrate Chemistry, Academic Press, New York (1963), Vol. 2, p. 320.
M. Fiorini, F. Marcati, and G. M. Giongo, J. Mol. Catal.,4, 125 (1978).
G. Pracejus and H. Pracejus, Tetrahedron Lett., 3497 (1977).
S. R. Landor, B. J. Miller, and A. R. Tatchell, J. Chem. Soc., C, 1822 (1966).
R. Huisgen and C. Ruchardt, Lieb. Ann. Chem.,601, 31 (1956).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 843–848, April, 1987.
Rights and permissions
About this article
Cite this article
Pavlov, V.A., Simonova, T.V. & Klabunovskii, E.I. Asymmetric reduction of the carbonyl group by chiral hydrides. 1. Stereochemical considerations. Russ Chem Bull 36, 770–775 (1987). https://doi.org/10.1007/BF00962317
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00962317