title: 6-Azabicyclo[3.2.1]octanes Via Copper-Catalyzed Enantioselective Alkene Carboamination.
abstract: Bridged bicyclic rings containing nitrogen heterocycles are important motifs in bioactive small organic molecules. An enantioselective copper-catalyzed alkene carboamination reaction that creates bridged heterocycles is reported herein. Two new rings are formed in this alkene carboamination reaction whereN-sulfonyl-2-aryl-4-pentenamines are converted to 6-azabicyclo[3.2.1]octanes using [Ph-Box-Cu](OTf)2or related catalysts in the presence of MnO2as stoichiometric oxidant in moderate to good yields and generally excellent enantioselectivities. Two new stereocenters are formed in the reaction, and the C-C bond-forming arene addition is a net C-H functionalization.
authors.affiliation: Department of Chemistry, The State University of New York at Buffalo, Buffalo, New York 14260, United States. ; phone: (+1)-715-645-4225.
authors.forename: Barbara J
authors.initials: BJ
authors.lastname: Casavant
authors.affiliation: Department of Chemistry, The State University of New York at Buffalo, Buffalo, New York 14260, United States. ; phone: (+1)-715-645-4225.
authors.forename: Azade S
authors.initials: AS
authors.lastname: Hosseini
authors.affiliation: Department of Chemistry, The State University of New York at Buffalo, Buffalo, New York 14260, United States. ; phone: (+1)-715-645-4225.
authors.forename: Sherry R
authors.initials: SR
authors.lastname: Chemler
keywords: 6-azabicyclo[3.2.1]octane; alkaloids; carboamination; copper-catalyzed; enantioselective