title: An anionic nucleophilic catalyst system for the diastereoselective synthesis of trans-beta-lactams.
abstract: Trans-disubstituted beta-lactams show increasing utility and prominence in numerous pharmaceutical applications, making their asymmetric synthesis an attractive goal for chemists. We introduce an anionic, nucleophilic catalyst system that provides an efficient, diastereoselective route to trans-disubstituted beta-lactams, a complement to our previously described catalytic methodology for generating the corresponding cis diastereomers. This catalytic, "switch mechanism" process allows for flexibility in the stereoselective synthesis of beta-lactams, producing either cis or trans products as desired from the same substrates. [reaction: see text]
authors.affiliation: Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, MD 21218, USA.
authors.forename: Anthony
authors.initials: A
authors.lastname: Weatherwax
authors.forename: Ciby J
authors.initials: CJ
authors.lastname: Abraham
authors.forename: Thomas
authors.initials: T
authors.lastname: Lectka
mesh_terms: D000838:Anions / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000838:Anions; D047090:beta-Lactams