1-CHLOROALKYL PARA-TOLYL SULFOXIDES AS ACETYLIDE ANION EQUIVALENT - A NOVEL SYNTHESIS INCLUDING ASYMMETRIC-SYNTHESIS OF PROPARGYLIC ALCOHOLS FROM CARBONYL-COMPOUNDS

被引：8

作者：

SATOH, T ^{[1
]}

HAYASHI, Y ^{[1
]}

YAMAKAWA, K ^{[1
]}

机构：

[1] SCI UNIV TOKYO, FAC PHARMACEUT SCI, ICHIGAYA FUNAGAWARA MACHI, SHINJUKU KU, TOKYO 162, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1991年 / 64卷 / 07期

关键词：

D O I：

10.1246/bcsj.64.2153

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Addition of the carbanion of 1-chloroalkyl p-tolyl sulfoxide to carbonyl compounds gave the adducts, which were heated in refluxing toluene or xylene to give vinyl chlorides in high overall yield. Dehydrochlorination of the vinyl chlorides with excess n-BuLi afforded propargylic alcohols in high yields. Asymmetric synthesis of both enantiomers of the propargylic alcohols was realized using optically active 1-chloroalkyl p-tolyl sulfoxide and aldehyde.

引用

页码：2153 / 2158

页数：6

共 27 条

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