Formation and utility of oxasilacyclopentenes derived from functionalized alkynes

被引：46

作者：

Clark, TB ^{[1
]}

Woerpel, KA ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 31期

关键词：

D O I：

10.1021/ja047498f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Oxasilacyclopentenes were shown to be synthetically useful masked allylic alcohols constructed in high yields and regioselectivities from terminal and internal alkynes. Several functional groups were shown to be tolerated utilizing silver-catalyzed silacyclopropenation of alkynes. In situ insertion of various carbonyl compounds into silacyclopropenes afforded regioselective formation of oxasilacyclopentenes. Elaboration of the oxasilacyclopentenes displayed the synthetic utility of these substrates. Both diastereoselective hydrogenation and Diels-Alder reactions utilizing the vinylsilane functionality demonstrated the reactivity and synthetic utility of oxasilacyclopentenes. Copyright © 2004 American Chemical Society.

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页码：9522 / 9523

页数：2

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