CHIRAL N,N-DIALKYLNOREPHEDRINES AS CATALYSTS OF THE HIGHLY ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALIPHATIC AND AROMATIC-ALDEHYDES - THE ASYMMETRIC-SYNTHESIS OF SECONDARY ALIPHATIC AND AROMATIC ALCOHOLS OF HIGH OPTICAL PURITY

被引:238
作者
SOAI, K
YOKOYAMA, S
HAYASAKA, T
机构
[1] Department of Applied Chemistry, Faculty of Science, Science University of Tokyo, Shinjuku
关键词
D O I
10.1021/jo00013a035
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The chiral N,N-dialkylnorephedrine-catalyzed addition of dialkylzincs to aliphatic and aromatic aldehydes afforded secondary alcohols of high optical purity (to > 95% ee). Among the N,N-di(primary alkyl)norephedrines, N,N-di-n-butylnorephedrine (DBNE, 3d) was found to be the most effective catalyst. 1-Phenyl-2-(1-pyrrolidinyl)propan-1-ol (3i) and N,N-diallylnorephedrine (3j) were also highly effective catalysts. The method described provides optically active secondary aliphatic alcohols of high optical purity which cannot be prepared by conventional methods.
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页码:4264 / 4268
页数:5
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