Coupling Reaction of Magnesium Alkylidene Carbenoids with α-Sulfonylallyllithiums: An Efficient Route to Multi-Substituted Vinylallenes

被引：19

作者：

Kimura, Tsutomu ^{[1
]}

Kobayashi, Gen ^{[2
]}

Ishigaki, Masashi ^{[2
]}

Inumaru, Mio ^{[2
]}

Sakurada, Jo ^{[2
]}

Satoh, Tsuyoshi ^{[1
,2
]}

机构：

[1] Tokyo Univ Sci, Dept Chem, Fac Sci, Shinjuku Ku, Tokyo 1620826, Japan

[2] Tokyo Univ Sci, Grad Sch Chem Sci & Technol, Shinjuku Ku, Tokyo 1620826, Japan

来源：

SYNTHESIS-STUTTGART | 2012年 / 44卷 / 23期

关键词：

vinylallenes; magnesium alkylidene carbenoids; allyl sulfones; vinyl sulfones; 1-chlorovinyl p-tolyl sulfoxides; coupling; DIELS-ALDER REACTION; CORRESPONDING ALLYLIC SULFONES; P-TOLYL SULFOXIDES; CARBON-CARBON BOND; VINYL-ALLENES; MULTICOMPONENT REACTIONS; ENYNE ACETATES; SYNTHETIC USES; LITHIUM; DERIVATIVES;

D O I：

10.1055/s-0032-1317507

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of vinylallenes were successfully synthesized from 1-chlorovinyl p-tolyl sulfoxides and allyl or vinyl sulfones. Allyl and vinyl sulfones served as alpha-sulfonylallyllithium sources were prepared from carbonyl compounds in three or four steps in good overall yields. The coupling reaction of alpha-sulfonylallyllithiums with magnesium alkylidene carbenoids, which were generated from 1-chlorovinyl p-tolyl sulfoxides and isopropylmagnesium chloride, afforded multi-substituted vinylallenes in up to 88% yield.

引用

页码：3623 / 3632

页数：10

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