title: Stereospecific and stereoselective alkyl and silylcyclopropanation of alpha,beta-unsaturated amides.
abstract: 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.
authors: 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. jmcg@uniovi.es
authors: José M
authors: JM
authors: Concellón
authors: Humberto
authors: H
authors: Rodríguez-Solla
authors: Carmen
authors: C
authors: Méjica
authors: Elena G
authors: EG
authors: Blanco
authors: Santiago
authors: S
authors: García-Granda
authors: M Rosario
authors: MR
authors: Díaz
mesh_terms: D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D017608:Chromium Compounds / Q000737:chemistry*; D003521:Cyclopropanes / Q000737:chemistry*; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000577:Amides; D002712:Chlorides; D017608:Chromium Compounds; D003521:Cyclopropanes; D012821:Silanes; C017133:chromous chloride