HIGHLY STEREOSELECTIVE PREPARATION OF TRI-SUBSTITUTED AND TETRA-SUBSTITUTED OLEFINS VIA BETA-TRIBUTYLSTANNYL-ALPHA,BETA-UNSATURATED KETONES

被引：26
|
作者：
TAKEDA, T
KABASAWA, Y
FUJIWARA, T
机构：
[1] Department of Applied Chemistry, Tokyo University of Agriculture and Technology, Koganei, Tokyo
来源：
TETRAHEDRON | 1995年 / 51卷 / 09期
关键词：
D O I：
10.1016/0040-4020(95)00016-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The palladium(0)-catalyzed reactions of beta-tributylstannyl-alpha,beta-unsaturated ketones 3 with benzyl or aryl halides in the presence of copper(I) iodide gave the tri- and tetra-substituted olefins 4 or 5 with high stereoselectivity, respectively. It was found that the yields of 5 were remarkably improved by the use of triethylamine as an additive. The starting materials 3 were easily prepared by the tin(IV) chloride-promoted coupling reaction of alpha-tributylstannylthioacetals with enol silyl ethers followed by the treatment with potassium hydride or DBU in good yields.
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页码：2515 / 2524
页数：10
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