title: Enantioselective CuH-catalyzed anti-Markovnikov hydroamination of 1,1-disubstituted alkenes.
abstract: Enantioselective synthesis of β-chiral amines has been achieved via copper-catalyzed hydroamination of 1,1-disubstituted alkenes with hydroxylamine esters in the presence of a hydrosilane. This mild process affords a range of structurally diverse β-chiral amines, including β-deuterated amines, in excellent yields with high enantioselectivities. Furthermore, catalyst loading as low as 0.4 mol% could be employed to deliver product in undiminished yield and selectivity, demonstrating the practicality of this method for large-scale synthesis.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
authors.forename: Shaolin
authors.initials: S
authors.lastname: Zhu
authors.forename: Stephen L
authors.initials: SL
authors.lastname: Buchwald
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D013237:Stereoisomerism; D020058:Styrene / Q000737:chemistry
chemical_list: D000475:Alkenes; D020058:Styrene; D003300:Copper; D006859:Hydrogen