title: Ni-Catalyzed Enantioselective C-Acylation of α-Substituted Lactams.
abstract: A new strategy for catalytic enantioselective C-acylation to generate α-quaternary-substituted lactams is reported. Ni-catalyzed three-component coupling of lactam enolates, benzonitriles, and aryl halides produces β-imino lactams that then afford β-keto lactams by acid hydrolysis. Use of a readily available Mandyphos-type ligand and addition of LiBr enable the construction of quaternary stereocenters on α-substituted lactams to form β-keto lactams in up to 94% ee.
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.
authors.forename: Masaki
authors.initials: M
authors.lastname: Hayashi
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.
authors.forename: Shoshana
authors.initials: S
authors.lastname: Bachman
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.
authors.forename: Satoshi
authors.initials: S
authors.lastname: Hashimoto
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.|Department of Chemistry and Biochemistry, Loyola University , Chicago, Illinois 60660, United States.
authors.forename: Chad C
authors.initials: CC
authors.lastname: Eichman
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.
authors.forename: Brian M
authors.initials: BM
authors.lastname: Stoltz
mesh_terms: D000215:Acylation; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D007769:Lactams / Q000737:chemistry*; D009532:Nickel / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007769:Lactams; D002244:Carbon; D009532:Nickel