Rhodium(II)-Catalyzed Stereoselective Synthesis of Allylsilanes

David M. Guptill, Carolyn M. Cohen and Huw M. L. Davies

Organic Letters,
2013, 15, (24), 6120-6123; 10.1021/ol4028978


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.

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