Asymmetric Michael reaction involving chiral imines/secondary enamines: stereocontrolled synthesis of 2,2-disubstituted tetrahydrothiophen-3-ones.
[reaction: see text] The asymmetric Michael reaction involving a chiral imine derived from 2-methyltetrahydrothiophenone-3-one and enantiopure (R)-1-phenylethylamine with a variety of electrophilic alkenes furnished 2,2-disubstituted tetrahydrothiophenone-3-ones with good yields and excellent stereoselectivity.
Desmaële
Didier
D
Unité de Chimie Organique associée au CNRS (UMR 8076) and Laboratoire de Cristallographie Bioinorganique, Centre d'Etudes Pharmaceutiques, Université Paris-Sud, 5 rue J.-B. Clément, 92296 Châtenay-Malabry, France. didier.desmaele@cep.u-psud.fr
Delarue-Cochin
Sandrine
S
Cavé
Christian
C
D'Angelo
Jean
J
Morgant
Georges
G
D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D007202:Indicators and Reagents; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism; D013876:Thiophenes / Q000032:analysis / Q000138:chemical synthesis*
D000588:Amines; D007202:Indicators and Reagents; D013876:Thiophenes