Enantioselective addition of diethylzinc to aldehydes catalyzed by chiral amino alcohols. Substituent effect and nonlinear effect

被引：27

作者：

Ohga, T

Umeda, S

Kawanami, Y ^{[1
]}

机构：

[1] Kagawa Univ, Fac Agr, Dept Biochem & Food Sci, Miki, Kagawa 7610795, Japan

[2] Kagawa Univ, Fac Educ, Dept Chem, Takamatsu, Kagawa 7608522, Japan

来源：

TETRAHEDRON | 2001年 / 57卷 / 23期

关键词：

catalysis; addition reaction; asymmetric induction; amino alcohols; nonlinear effect;

D O I：

10.1016/S0040-4020(01)00423-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new series of chiral beta -amino alcohols derived from (S)-leucine, valine, and phenylalanine have been synthesized and evaluated as chiral catalysts for the enantioselective addition of diethylzinc to aldehydes. The beta -amino alcohol (1c) possessing a isobutyl substituent and two phenethyl substituents on the carbinol carbon atom was found to be an efficient and optimal Ligand to catalyze the diethylzinc addition with high enantioselectivity (up to 97% ee) and good yield. Furthermore, a strong (+)-nonlinear effect (asymmetric amplification) was observed in the enantioselective catalysis, providing high level of enantioselection (93% ee) by use of ligand 1c in 20% ee. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：4825 / 4829

页数：5

共 14 条

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[2]

2-1

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