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

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

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 stereoselectivi...

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Veröffentlicht in:Organic letters 2008-01, Vol.10 (2), p.349-352
Hauptverfasser: Concellón, José M, Rodríguez-Solla, Humberto, Méjica, Carmen, Blanco, Elena G, García-Granda, Santiago, Díaz, M. Rosario
Format: Artikel
Sprache:eng
Schlagworte:
Amides - chemistry
Catalysis
Chlorides - chemistry
Chromium Compounds - chemistry
Cyclopropanes - chemistry
Molecular Structure
Silanes - chemistry
Stereoisomerism
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol702876r