American Chemical Society
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Stereospecific and Stereoselective Alkyl and Silylcyclopropanation of α,β-Unsaturated Amides

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posted on 2008-01-17, 00:00 authored by José M. Concellón, Humberto Rodríguez-Solla, Carmen Méjica, Elena G. Blanco, Santiago García-Granda, M. Rosario Díaz
A novel chromium-promoted alkyl- and silyl cyclopropanation of (E)- or (Z)-α,β-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.