Stereospecific and stereoselective alkyl and silylcyclopropanation of alpha,beta-unsaturated amides.
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.
Concellón
José M
JM
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
Rodríguez-Solla
Humberto
H
Méjica
Carmen
C
Blanco
Elena G
EG
García-Granda
Santiago
S
Díaz
M Rosario
MR
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
D000577:Amides; D002712:Chlorides; D017608:Chromium Compounds; D003521:Cyclopropanes; D012821:Silanes; C017133:chromous chloride