title: A highly stereoselective synthesis of chiral alpha-amino-beta-lactams via the Kinugasa reaction employing ynamides.
abstract: A highly stereoselective synthesis of chiral alpha-amino-beta-lactam through an ynamide-Kinugasa reaction is described. In addition, a mechanistic model is illustrated here to rationalize the observed diastereoselectivity, which depends on both the initial [3 + 2] cycloaddition step and the subsequent protonation for which both are highly selective.
authors.affiliation: Division of Pharmaceutical Sciences and Department of Chemistry, 777 Highland Avenue, University of Wisconsin, Madison, Wisconsin 53705-2222, USA.
authors.forename: Xuejun
authors.initials: X
authors.lastname: Zhang
authors.forename: Richard P
authors.initials: RP
authors.lastname: Hsung
authors.forename: Hongyan
authors.initials: H
authors.lastname: Li
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhang
authors.forename: Whitney L
authors.initials: WL
authors.lastname: Johnson
authors.forename: Ruth
authors.initials: R
authors.lastname: Figueroa
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000480:Alkynes; D000577:Amides; D047090:beta-Lactams