Efficient one-pot synthesis of 1-chlorovinyl p-tolyl sulfoxides from aldehydes and ketones by the Horner-Wadsworth-Emmons reaction

被引：4

作者：

Kimura, Tsutomu ^{[1
]}

Kobayashi, Gen ^{[1
]}

Ijima, Shiori ^{[1
]}

Saito, Sae ^{[1
]}

Imafuji, Aki ^{[1
]}

Satoh, Tsuyoshi ^{[1
]}

机构：

[1] Tokyo Univ Sci, Grad Sch Sci, Dept Chem, Tokyo, Japan

来源：

HETEROATOM CHEMISTRY | 2017年 / 28卷 / 05期

关键词：

1-chlorovinyl p-tolyl sulfoxide; Fritsch-Buttenberg-Wiechell rearrangement; Horner-Wadsworth-Emmons reaction; magnesium alkylidene carbenoid; one-pot synthesis; MAGNESIUM ALKYLIDENE CARBENOIDS; INCLUDING ASYMMETRIC-SYNTHESIS; ALPHA-PHOSPHORYL SULFOXIDES; NUCLEOPHILIC-SUBSTITUTION; WIECHELL REARRANGEMENT; CONSECUTIVE REACTION; ELECTROPHILIC NATURE; CONJUGATE ADDITION; LITHIUM ACETYLIDES; WITTIG SYNTHESIS;

D O I：

10.1002/hc.21395

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A variety of 2-monosubstituted and 2,2-disubstituted 1-chlorovinyl p-tolyl sulfoxides was synthesized through a one-pot procedure by the Horner-Wadsworth-Emmons reaction of carbonyl compounds with [chloro(diethoxyphosphoryl)(p-tolylsulfinyl)methyl]lithium, which was generated from diethyl chlorophosphate, chloromethyl p-tolyl sulfoxide, and lithium diisopropylamide in advance. The in situ-prepared sulfoxides were directly converted into alkynes via the sulfoxide/magnesium exchange reaction with i-PrMgCl and the subsequent Fritsch-Buttenberg-Wiechell rearrangement of the resulting magnesium alkylidene carbenoids.

引用

页数：6

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