Transition metal-catalyzed [5+2] cycloadditions of 2-substituted-1-vinylcyclopropanes: Catalyst control and reversal of regioselectivity

被引：77

作者：

Wender, PA ^{[1
]}

Dyckman, AJ ^{[1
]}

机构：

[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 13期

关键词：

D O I：

10.1021/ol991171f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Studies on the stereo- and regioselectivity of rhodium(I) catalyzed [5 + 2] cycloadditions of 2-substituted-1-vinylcyclopropanes are described. The relative stereochemistry of vicinal cyclopropane substituents is found to be conserved in these reactions, translating into distinct 1,4- or 1,5-stereorelationships in the cycloadducts. Exceptional regioselectivity in cyclopropane bond cleavage and even reversal of cleavage selectivity can be obtained through judicious selection of substituents and/or catalyst.

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页码：2089 / 2092

页数：4

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