Novel carbon-carbon bond-forming reactions using carbocations produced from substituted propargyl silyl ethers by the action of TMSOTf

被引：55

作者：

Ishikawa, T ^{[1
]}

Okano, M ^{[1
]}

Aikawa, T ^{[1
]}

Saito, S ^{[1
]}

机构：

[1] Okayama Univ, Fac Engn, Dept Biosci & Biotechnol, Okayama 7008530, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 13期

关键词：

D O I：

10.1021/jo010157p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly useful carbon-carbon bond forming reactions using stable allenyl, propargyl, or allyl-propargyl hybrid cations have been developed. These carbocations could be generated from silyl 1-(pi -donor)-substituted propargyl ethers by the action of trimethylsilyl trifluoromethanesulfonate in dichloromethane at -78 degreesC to room temperature and could be attacked nucleophilically by electron rich arenes, allylsilanes, or enol silyl ethers, giving rise to allenes, alkynes, and their derivatives. A novel method for regio- and stereoselective synthesis of conjugated enynes utilizing allyl-propargyl hybrid cations has also been established.

引用

页码：4635 / 4642

页数：8

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