title: Copper-catalyzed stereoselective aminoboration of bicyclic alkenes.
abstract: A copper-catalyzed aminoboration of bicyclic alkenes, including oxa- and azabenzonorbornadienes, has been developed. With this method, amine and boron moieties are simultaneously introduced at an olefin with exo selectivity. Subsequent stereospecific transformations of the boryl group can provide oxygen- and nitrogen-rich cyclic molecules with motifs that may be found in natural products or pharmaceutically active compounds. Moreover, a catalytic asymmetric variant of this transformation was realized by using a copper complex with a chiral bisphosphine ligand, namely (R,R)-Ph-BPE.
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan).
authors.forename: Ryosuke
authors.initials: R
authors.lastname: Sakae
authors.forename: Koji
authors.initials: K
authors.lastname: Hirano
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Satoh
authors.forename: Masahiro
authors.initials: M
authors.lastname: Miura
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001643:Bridged Bicyclo Compounds; D003300:Copper
keywords: alkenes; aminoboration; copper; synthetic methods; umpolung