AMINOBOROHYDRIDES .2. REGIOSPECIFIC REDUCTIONS OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS WITH LITHIUM PYRROLIDINOBOROHYDRIDE - A FACILE CONVERSION OF ALPHA,BETA-UNSATURATED ALDEHYDES AND KETONES TO THE CORRESPONDING ALLYLIC ALCOHOLS IN HIGH-PURITY

被引：59

作者：

FULLER, JC ^{[1
]}

STANGELAND, EL ^{[1
]}

GORALSKI, CT ^{[1
]}

SINGARAM, B ^{[1
]}

机构：

[1] UNIV CALIF SANTA CRUZ,DEPT CHEM & BIOCHEM,SANTA CRUZ,CA 95064

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 02期

关键词：

D O I：

10.1016/S0040-4039(00)60561-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lithium aminoborohydrides (LiABH3), obtained by the reaction of n-BuLi with amine-boranes, are powerful reducing agents for the reduction of alpha,beta-unsaturated aldehydes and ketones to the corresponding allylic alcohols. Thus, lithium pyrrolidinoborohydride (LiPyrrBH3) reduces cinnamaldehyde and cyclohexenone to give exclusively cinnamyl alcohol and 2-cyclohexen-1-ol respectively. This 1,2-reduction appears to be general and ester groups are tolerated. The yield of allylic alcohols from this procedure is essentially quantitative.

引用

页码：257 / 260

页数：4

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