ENANTIOSELECTIVE ADDITION OF DIORGANOZINCS TO ALDEHYDES CATALYZED BY BETA-AMINO ALCOHOLS

被引：221

作者：

NOYORI, R ^{[1
]}

SUGA, S ^{[1
]}

KAWAI, K ^{[1
]}

OKADA, S ^{[1
]}

KITAMURA, M ^{[1
]}

OGUNI, N ^{[1
]}

HAYASHI, M ^{[1
]}

KANEKO, T ^{[1
]}

MATSUDA, Y ^{[1
]}

机构：

[1] YAMAGUCHI UNIV,FAC SCI,DEPT CHEM,YAMAGUCHI 753,JAPAN

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1990年 / 382卷 / 1-2期

关键词：

D O I：

10.1016/0022-328X(90)85212-H

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Nucleophilic addition of dialkylzincs to aldehydes in hydrocarbon solvents is markedly accelerated by the presence of a catalytic amount of a β-dialkylamino alcohol. Use of certain sterically constrained chiral amino alcohols such as 3-exo-(dimethylamino)isoborneol or 1-t-butyl-2-piperidinoethanol effects highly enantioselective catalysis giving secondary alcohols in up to 99% ee. Dimethyl-, diethyl-, di-n-butyl-, and di-n-pentyl-zincs have been employed for the alkylation of substituted benzaldehydes and some olefinic or aliphatic aldehydes. Configurational correlation between the chiral auxiliary and alkylation products is discussed. © 1990.

引用

页码：19 / 37

页数：19

共 70 条

[1] ABSOLUTE CONFIGURATION OF ALPHA- AND BETA-METHYLCHOLINE ISOMERS AND THEIR ACETYL AND SUCCINYL ESTERS [J].