REDUCTION OF ALPHA-TRIALKYLSILOXY NITRILES WITH DIISOBUTYLALUMINIUM HYDRIDE (DIBAH) - A FACILE PREPARATION OF ALPHA-TRIALKYLSILOXY ALDEHYDES AND THEIR DERIVATIVES

被引：26

作者：

HAYASHI, M ^{[1
]}

YOSHIGA, T ^{[1
]}

NAKATANI, K ^{[1
]}

ONO, K ^{[1
]}

OGUNI, N ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 1994年 / 50卷 / 09期

关键词：

D O I：

10.1016/S0040-4020(01)86995-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stepwise synthesis of alpha-trimethylsiloxy aldehydes and alpha-hydroxy aldehydes could be acheived via the reduction of alpha-trimethylsiloxy nitriles with diisobuytylaluminium hydride (DIBAH) starting from a variety of ketones. The facile synthesis of optically active alpha-tert-butyldimethylsiloxy aldehydes was attained by combination of asymmetric silylcyanation of aldehydes and DIBAH reduction of optically active alpha-siloxy nitriles. Furthermore, in the reduction of some alpha-tert-butyldimethylsiloxy-beta,gamma-unsaturated nitriles, migration of the double bond took place to form more stable alpha-siloxy-alpha,beta-unsaturated aldehydes under some reactions conditions.

引用

页码：2821 / 2830

页数：10

共 28 条

[21] PREPARATION OF CHIRAL CYANOHYDRINS BY AN OXYNITRILASE-MEDIATED TRANSCYANATION [J].