title: Regioselective, Asymmetric Formal Hydroamination of Unactivated Internal Alkenes.
abstract: We report the regioselective and enantioselective formal hydroamination of unsymmetrical internal alkenes catalyzed by a copper catalyst ligated by DTBM-SEGPHOS. The regioselectivity of the reaction is controlled by the electronic effects of ether, ester, and sulfonamide groups in the homoallylic position. The observed selectivity underscores the influence of inductive effects of remote substituents on the selectivity of catalytic processes occurring at hydrocarbyl groups, and the method provides direct access to various 1,3-aminoalcohol derivatives with high enantioselectivity.
authors.affiliation: Department of Chemistry, University of California, Berkeley, CA 94720 (USA).|Division of Chemical Sciences, Lawrence Berkeley National Laboratory, Berkeley, CA 94720 (USA).
authors.forename: Yumeng
authors.initials: Y
authors.lastname: Xi
authors.affiliation: Department of Chemistry, University of California, Berkeley, CA 94720 (USA).
authors.forename: Trevor W
authors.initials: TW
authors.lastname: Butcher
authors.affiliation: Department of Chemistry, University of California, Berkeley, CA 94720 (USA).|Division of Chemical Sciences, Lawrence Berkeley National Laboratory, Berkeley, CA 94720 (USA).
authors.forename: Jing
authors.initials: J
authors.lastname: Zhang
authors.affiliation: Department of Chemistry, University of California, Berkeley, CA 94720 (USA). jhartwig@berkeley.edu.|Division of Chemical Sciences, Lawrence Berkeley National Laboratory, Berkeley, CA 94720 (USA). jhartwig@berkeley.edu.
authors.forename: John F
authors.initials: JF
authors.lastname: Hartwig
keywords: electronic effects; enantioselectivity; hydroamination; regioselectivity; unactivated internal olefins