title: Copper-catalyzed enantioselective allylic substitution with alkylboranes.
abstract: The first catalytic enantioselective allylic substitution reaction with alkylboron compounds has been achieved. The reaction between alkyl-9-BBN reagents and primary allylic chlorides proceeded with excellent γ-selectivities and high enantioselectivities under catalysis of a Cu(I)-DTBM-SEGPHOS system. The protocol produces terminal alkenes with an allylic stereogenic center branched with functionalized sp(3)-alkyl groups. The reaction with a γ-silicon-substituted allyl chloride affords an efficient strategy for the enantioselective synthesis of functionalized α-stereogenic chiral allylsilanes.
authors.affiliation: Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo, Japan.
authors.forename: Yoshinori
authors.initials: Y
authors.lastname: Shido
authors.forename: Mika
authors.initials: M
authors.lastname: Yoshida
authors.forename: Masahito
authors.initials: M
authors.lastname: Tanabe
authors.forename: Hirohisa
authors.initials: H
authors.lastname: Ohmiya
authors.forename: Masaya
authors.initials: M
authors.lastname: Sawamura
mesh_terms: D000475:Alkenes / Q000737:chemistry; D000498:Allyl Compounds / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000498:Allyl Compounds; D001880:Boranes; D009942:Organometallic Compounds; D012821:Silanes; D003300:Copper