title: Catalytic, Enantioselective, Intramolecular Sulfenoamination of Alkenes with Anilines.
abstract: A method for the catalytic, enantioselective, intramolecular sulfenoamination of alkenes with aniline nucleophiles has been developed. The method employs a chiral, Lewis basic selenophosphoramide catalyst and a Brønsted acid co-catalyst to promote stereocontrolled C-N and C-S bond formation by activation of an achiral sulfenylating agent. Benzoannulated nitrogen-containing heterocycles such as indolines, tetrahydroquinolines, and tetrahydrobenzazepines were prepared with high to excellent enantioselectivities. The impact of tether length and electron density of both the nucleophile and olefin on the reactivity, site selectivity, and enantioselectivity were investigated and interpreted in terms of substrate-dependent stereodetermining thiiranium ion formation or capture.
authors.affiliation: Roger Adams Laboratory, Department of Chemistry, University of Illinois , Urbana, Illinois 61801, United States.
authors.forename: Scott E
authors.identifier: 0000-0002-1099-9765
authors.initials: SE
authors.lastname: Denmark
authors.affiliation: Roger Adams Laboratory, Department of Chemistry, University of Illinois , Urbana, Illinois 61801, United States.
authors.forename: Hyung Min
authors.initials: HM
authors.lastname: Chi
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D058115:Lewis Bases / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000814:Aniline Compounds; D058115:Lewis Bases