title: Diastereo- and enantioselective copper-catalyzed intramolecular carboamination of alkenes for the synthesis of hexahydro-1H-benz[f]indoles.
abstract: A new method for the enantioselective synthesis of hexahydro-1H-benz[f]indoles is described. This copper-catalyzed enantioselective intramolecular alkene carboamination process can install vicinal tertiary and quaternary carbon stereocenters with high levels of diastereo- and enantioselectivity. The C-C bond-forming component of the reaction constitutes a C-H functionalization and no electronic activation of the aryl ring that undergoes addition is required. A known 5-HT(1A) receptor antagonist was synthesized efficiently using this method.
authors.affiliation: Department of Chemistry, The University at Buffalo, The State University of New York, Buffalo, New York 14260, United States.
authors.forename: Lei
authors.initials: L
authors.lastname: Miao
authors.forename: Imranul
authors.initials: I
authors.lastname: Haque
authors.forename: Maria R
authors.initials: MR
authors.lastname: Manzoni
authors.forename: Weng Siong
authors.initials: WS
authors.lastname: Tham
authors.forename: Sherry R
authors.initials: SR
authors.lastname: Chemler
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D001554:Benzene / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D007211:Indoles; D002244:Carbon; D003300:Copper; D006859:Hydrogen; D001554:Benzene