A benzannulation strategy for the synthesis of phenols and heteroaromatic compounds based on the reaction of (trialkylsilyl)vinylketenes with lithium ynolates

被引：35

作者：

Austin, Wesley F. ^{[1
]}

Zhang, Yongjun ^{[1
]}

Danheiser, Rick L. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

TETRAHEDRON | 2008年 / 64卷 / 05期

关键词：

(Trialkylsilyl)vinylketenes; benzannulation; ynolates; electrocyclic ring closure;

D O I：

10.1016/j.tet.2007.10.113

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(Trialkylsilyl)vinylketenes react with lithium ynolates to generate 3-(oxido)dienylketenes, which undergo rapid 6 pi-electrocyclization. The ultimate products of this benzannulation are highly substituted resorcinol monosilyl ethers, which are formed via a [1,3] carbon to oxygen silyl group shift. Further transformations of the benzannulation products are described providing efficient access to ortho-benzoquinones and benzofuran, benzoxepine, and benzoxocine ring systems. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：915 / 925

页数：11

共 56 条

[21] Stereoselective synthesis of highly substituted cyclopentenones through [4+1] annulations of trialkylsilyl vinyl ketenes with α-benzotriazolyl organolithium compounds [J].