title: Catalytic enantioselective alkene aminohalogenation/cyclization involving atom transfer.
abstract: Problem solved: the title reaction was used for the synthesis of chiral 2-bromo, chloro, and iodomethyl indolines and 2-iodomethyl pyrrolidines. Stereocenter formation is believed to occur by enantioselective cis aminocupration and C-X bond formation is believed to occur by atom transfer. The ultility of the products as versatile synthetic intermediates was demonstrated, as was a radical cascade cyclization sequence.
authors.affiliation: Department of Chemistry, The State University of New York at Buffalo, 14260, USA.
authors.forename: Michael T
authors.initials: MT
authors.lastname: Bovino
authors.forename: Sherry R
authors.initials: SR
authors.lastname: Chemler
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D054879:Halogenation; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry; D008670:Metals / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D007211:Indoles; D008670:Metals; D011759:Pyrrolidines; C057812:indoline; D003300:Copper