title: Highly enantioselective alkynylation of trifluoropyruvate with alkynylsilanes catalyzed by the BINAP-Pd complex: access to α-trifluoromethyl-substituted tertiary alcohols.
abstract: A highly enantioselective alkynylation catalyzed by the dicationic (S)-BINAP-Pd complex with a variety of alkynylsilanes and trifluoropyruvate is described. The catalytic reaction is applicable to highly enantioselective addition of polyyne to trifluoropyruvate to construct α-trifluoromethyl-substituted tertiary alcohols as enantiomerically enriched forms. The alkynyl products can be converted into a chiral allene bearing a trifluoromethyl group.
authors.affiliation: Department of Applied Chemistry, Tokyo Institute of Technology, Tokyo 152-8552, Japan.
authors.forename: Kohsuke
authors.initials: K
authors.lastname: Aikawa
authors.forename: Yūta
authors.initials: Y
authors.lastname: Hioki
authors.forename: Koichi
authors.initials: K
authors.lastname: Mikami
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D017611:Fluorine Compounds / Q000737:chemistry*; D007854:Lead / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D011773:Pyruvates / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000480:Alkynes; C406943:BINAP, 2-naphthol; D017611:Fluorine Compounds; D009281:Naphthalenes; D011773:Pyruvates; D012821:Silanes; D007854:Lead