title: Triclorosilane-mediated stereoselective synthesis of β-amino esters and their conversion to highly enantiomerically enriched β-lactams.
abstract: A highly stereoselective trichlorosilane-mediated reduction of N-benzyl enamines was developed; the combination of a low cost, easy to make metal-free catalyst and an inexpensive chiral auxiliary allowed to perform the reaction on substrates with different structural features often with total control of the stereoselectivity. By easy deprotection through hydrogenolysis followed by conversion of β-aminoester to 2-azetidinones, the synthesis of enantiomerically pure β-lactams (>98% e.e.) was successfully accomplished.
authors.affiliation: Dipartimento di Chimica Organica e Industriale-Universita' degli Studi di Milano, Via Golgi 19, I-20133 Milano, Italy.
authors.forename: Stefania
authors.initials: S
authors.lastname: Guizzetti
authors.forename: Maurizio
authors.initials: M
authors.lastname: Benaglia
authors.forename: Martina
authors.initials: M
authors.lastname: Bonsignore
authors.forename: Laura
authors.initials: L
authors.lastname: Raimondi
mesh_terms: D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis*
chemical_list: D000588:Amines; D004952:Esters; D012821:Silanes; D047090:beta-Lactams