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.
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页数：6
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