HIGHLY STEREOSELECTIVE SYNTHESIS OF TRISUBSTITUTED ETHYLENES FROM ALPHA-TRIALKYLSILYL KETONES

被引：33

作者：

OBAYASHI, M ^{[1
]}

UTIMOTO, K ^{[1
]}

NOZAKI, H ^{[1
]}

机构：

[1] KYOTO UNIV, DEPT IND CHEM, KYOTO 606, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1979年 / 52卷 / 06期

关键词：

D O I：

10.1246/bcsj.52.1760

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel procedure for preparing trisubstituted ethylenes stereoselectively is based on the reaction of α-trialkyl-silyl-substituted ketones with alkyllithium reagents and on the following highly discriminative elimination of the silyl and oxido (or hydroxyl) groups from the resulting adducts. The syn-elimination of both groups is observed under basic conditions, while the reaction proceeds in anti-idishion on acid treatment. Furthermore a-trimethyl-silylated ketones are shown to be readily obtained from 2-trimethylsilyl-2,3-dialkyloxiranes. The reaction sequence is applied to the stereoselective synthesis of tetrahomonerol which has been obtained from the codling moth.

引用

页码：1760 / 1764

页数：5

共 30 条

[1]

ARORA AS, 1972, METHODEN ORGANISCHEN, V5, P728

[2] SYNTHESIS OF NATURAL ISOMER OF A TETRAHOMOTERPENE ALCOHOL OBTAINED FROM CODLING MOTH [J].