Stereoselective synthesis of unsymmetrical conjugated dienes and trienes utilizing silacyclobutenes

被引：24
|
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.
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页码：3671 / 3675
页数：5
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