Asymmetric synthesis of beta-substituted alpha-methyl-beta-amino esters by Mannich reaction of (S,S)-(+)-pseudoephedrine acetamide derived enolate with imines.
[reaction: see text]. The reaction of an (S,S)-(+)-pseudoephedrine acetamide based enolate with several imines afforded smoothly and with full stereochemical control a series of beta-substituted alpha-methyl-beta-aminoamides that upon hydrolysis/esterification afforded the corresponding beta-aminoester derivatives in good yields and in almost enantiomerically pure form.
Departamento de Química Orgánica II, Facultad de Ciencias, Universidad del País Vasco-Euskal Herriko Unibertsitatea, P.O. Box E-644, 48080 Bilbao, Spain.
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D000081:Acetamides / Q000138:chemical synthesis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D004809:Ephedrine / Q000031:analogs & derivatives* / Q000737:chemistry*; D006868:Hydrolysis; D007097:Imines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D013237:Stereoisomerism
D000081:Acetamides; D007097:Imines; D004809:Ephedrine