Organic letters

Rhodium (II)-Catalyzed Stereoselective Synthesis of Allylsilanes

DM Guptill, CM Cohen, HML Davies

Index: Guptill, David M.; Cohen, Carolyn M.; Davies, Huw M. L. Organic Letters, 2013 , vol. 15, # 24 p. 6120 - 6123

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Citation Number: 6

Abstract

The rhodium-catalyzed decomposition of 2-(triisopropylsilyl) ethyl aryl-and vinyldiazoacetates results in the stereoselective formation of Z-allylsilanes. The transformation is considered to proceed by silyl-directed intramolecular C–H functionalization to form a β-lactone intermediate followed by a silyl-activated extrusion of carbon dioxide.