title: Copper-Catalyzed Divergent Addition Reactions of Enoldiazoacetamides with Nitrones.
abstract: Catalyst-controlled divergent addition reactions of enoldiazoacetamides with nitrones have been developed. By using copper(I) tetrafluoroborate/bisoxazoline complex as the catalyst, a [3+3]-cycloaddition reaction was achieved with excellent yield and enantioselectivity under exceptionally mild conditions, which represents the first highly enantioselective base-metal-catalyzed vinylcarbene transformation. When the catalyst was changed to copper(I) triflate, Mannich addition products were formed in high yields with near exclusivity under otherwise identical conditions.
authors.affiliation: Department of Chemistry, The University of Texas at San Antonio , San Antonio, Texas 78249, United States.
authors.forename: Qing-Qing
authors.initials: QQ
authors.lastname: Cheng
authors.affiliation: Department of Chemistry, The University of Texas at San Antonio , San Antonio, Texas 78249, United States.
authors.forename: Julietta
authors.initials: J
authors.lastname: Yedoyan
authors.affiliation: Department of Chemistry, The University of Texas at San Antonio , San Antonio, Texas 78249, United States.
authors.forename: Hadi
authors.initials: H
authors.lastname: Arman
authors.affiliation: Department of Chemistry, The University of Texas at San Antonio , San Antonio, Texas 78249, United States.
authors.forename: Michael P
authors.initials: MP
authors.lastname: Doyle
mesh_terms: D000081:Acetamides / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D013237:Stereoisomerism
chemical_list: D000081:Acetamides; D003300:Copper