title: Enantioselective synthesis of α-aminosilanes by copper-catalyzed hydroamination of vinylsilanes.
abstract: The synthesis of α-aminosilanes by a highly enantio- and regioselective copper-catalyzed hydroamination of vinylsilanes is reported. The system employs Cu-DTBM-SEGPHOS as the catalyst, diethoxymethylsilane as the stoichiometric reductant, and O-benzoylhydroxylamines as the electrophilic nitrogen source. This hydroamination reaction is compatible with differentially substituted vinylsilanes, thus providing access to amino acid mimics and other valuable chiral organosilicon compounds.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139 (USA).
authors.forename: Nootaree
authors.initials: N
authors.lastname: Niljianskul
authors.forename: Shaolin
authors.initials: S
authors.lastname: Zhu
authors.forename: Stephen L
authors.initials: SL
authors.lastname: Buchwald
mesh_terms: D000586:Amination; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D012821:Silanes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D000588:Amines; D012821:Silanes; D014753:Vinyl Compounds; C476909:vinylsilane; D003300:Copper
keywords: asymmetric synthesis; copper; hydroamination; silicon