Rhodium-Catalyzed Enantioselective Vinylogous Addition of Enol Ethers to Vinyldiazoacetates

被引：68

作者：

Smith, Austin G. ^{[1
]}

Davies, Huw M. L. ^{[1
]}

机构：

[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 44期

基金：

美国国家卫生研究院;

关键词：

REACTIVITY; CYCLOADDITION;

D O I：

10.1021/ja3092399

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly asymmetric vinylogous addition of acyclic silyl enol ethers to siloxyvinyldiazoacetate is described. The reaction features a diastereoselective 1,4-siloxy group migration event. Products are obtained in up to 97% ee. When more sterically crowded silyl enol ethers are employed, an enantioselective formal [3+2] cyclo-addition becomes the dominant reaction pathway. Control experiments reveal the (Z)-olefin geometry to be critical for high levels of enantiocontrol.

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收藏

页码：18241 / 18244

页数：4

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