Stereoselective synthesis of unsymmetrical conjugated dienes and trienes utilizing silacyclobutenes

被引：26

作者：

Jin, Chung Keun

Yamada, Toshiaki

Sano, Shigeki

Shiro, Motoo

Nagao, Yoshimitsu ^{[1
]}

机构：

[1] Univ Tokushima, Grad Sch Pharmaceut Sci, Tokushima 7708505, Japan

[2] Rigaku Corp, Tokyo 1968666, Japan

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 21期

基金：

日本学术振兴会;

关键词：

dialkynyldiarylsilane; zirconium complex; silacyclobutene; tetrabutylammonium fluoride; conjugated diene;

D O I：

10.1016/j.tetlet.2007.03.122

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of the different kinds of alkynyl-substituted dialkynyldiarylsilanes with zirconocene-ethylene complex CPZZr(CHZ=CHz) followed by acidification with 3 N HCl gave regio- and stereo selectively the corresponding silacyclobutenes in good yields. Desilylation of the silacyclobutenes with tetrabutylammonium fluoride afforded stereoselectively unsymmetrical conjugated (1E,3E)-dienes and -trienes (R-1 or R-2 = 1-cyclohexenyl) in excellent yields. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：3671 / 3675

页数：5