title: Diverse Asymmetric Hydrofunctionalization of Aliphatic Internal Alkenes through Catalytic Regioselective Hydroboration.
abstract: We report a two-step strategy for diverse hydrofunctionalizations of aliphatic internal alkenes with high regioselectivity and enantioselectivity. This process comprises a copper-catalyzed asymmetric hydroboration and subsequent stereospecific derivatizations of the secondary boronates. By this strategy, a range of compounds, such as amides, alkyl fluorides and bromides, alcohols, aldehydes, arenes, and heteroarenes, were synthesized from an internal alkene with high regioselectivity and enantioselectivity. Computational studies provide insight into the origins of these selectivities.
authors.affiliation: Division of Chemical Sciences, Lawrence Berkeley National Laboratory, and Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: Yumeng
authors.initials: Y
authors.lastname: Xi
authors.affiliation: Division of Chemical Sciences, Lawrence Berkeley National Laboratory, and Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: John F
authors.initials: JF
authors.lastname: Hartwig
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C578864:4,4,5,5-tetramethyl(1,3,2)dioxaborolane; D000475:Alkenes; D001896:Boron Compounds; D003300:Copper