title: Lewis base catalyzed, enantioselective, intramolecular sulfenoamination of olefins.
abstract: A method for the enantioselective, intramolecular sulfenoamination of various olefins has been developed using a chiral BINAM-based selenophosphoramide, Lewis base catalyst. Terminal and trans disubstituted alkenes afforded pyrrolidines, piperidines, and azepanes in high yields and high enantiomeric ratios via enantioselective formation and subsequent stereospecific capture of the thiiranium intermediate with the pendant tosyl-protected amine.
authors.affiliation: Department of Chemistry, University of Illinois Urbana-Champaign , Urbana, Illinois 61801, United States.
authors.forename: Scott E
authors.initials: SE
authors.lastname: Denmark
authors.forename: Hyung Min
authors.initials: HM
authors.lastname: Chi
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D058115:Lewis Bases / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001381:Azepines; D058115:Lewis Bases; D010880:Piperidines; D011759:Pyrrolidines