Stereospecific and stereoselective alkyl and silylcyclopropanation of alpha,beta-unsaturated amides.

Org Lett

Departamento de Química Orgánica e Inorgánica, and Departamento de Química Física y Analítica, Facultad de Química, Universidad de Oviedo, Julián Clavería 8, 33071 Oviedo, Spain.

Published: January 2008

A novel chromium-promoted alkyl- and silyl cyclopropanation of (E)- or (Z)-alpha,beta-unsaturated amides in which the C-C double bond is di-, or trisubstituted is described. This process takes place with total stereospecificity, and the new stereogenic center is generated with high or total stereoselectivity. A mechanism is proposed to explain the cyclopropanation reaction.

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Source
http://dx.doi.org/10.1021/ol702876rDOI Listing

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