title: Copper-Catalyzed Enantioselective Addition of Styrene-Derived Nucleophiles to Imines Enabled by Ligand-Controlled Chemoselective Hydrocupration.
abstract: The copper-catalyzed intermolecular enantioselective addition of styrenes to imines has been achieved under mild conditions at ambient temperature. This process features the use of styrenes as latent carbanion equivalents via the intermediacy of catalytically generated benzylcopper derivatives, providing an effective means for accessing highly enantiomerically enriched amines bearing contiguous stereocenters. Mechanistic studies shed light on the origin of the preferential styrene hydrocupration in the presence of an imine with the Ph-BPE-derived copper catalyst.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
authors.forename: Yang
authors.initials: Y
authors.lastname: Yang
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
authors.forename: Ian B
authors.initials: IB
authors.lastname: Perry
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
authors.forename: Stephen L
authors.initials: SL
authors.lastname: Buchwald
mesh_terms: D000588:Amines; D002384:Catalysis; D002626:Chemistry, Pharmaceutical; D003300:Copper / Q000737:chemistry*; D006838:Hydrocarbons / Q000737:chemistry; D007097:Imines / Q000737:chemistry; D008024:Ligands; D015394:Molecular Structure; D013237:Stereoisomerism; D020058:Styrene / Q000737:chemistry*; D013343:Styrenes / Q000737:chemistry*; D013379:Substrate Specificity; D013696:Temperature
chemical_list: D000588:Amines; D006838:Hydrocarbons; D007097:Imines; D008024:Ligands; D013343:Styrenes; D020058:Styrene; D003300:Copper