title: A new entry to Pd-H chemistry: catalytic asymmetric conjugate reduction of enones with EtOH and a highly enantioselective synthesis of warfarin.
abstract: [reaction: see text] We report here the catalytic asymmetric conjugate reduction of enones using ethanol as a hydride source. The reaction was carried out in the presence of a chiral Pd complex at ambient temperature in ethanol, and the desired products were obtained in high chemical yield and high enantioselectivity. We applied this novel reaction to the catalytic asymmetric synthesis of warfarin (96% ee), and on the basis of d-labeling experiments, the reaction mechanism is proposed.
authors.affiliation: RIKEN (The Institute of Physical and Chemical Research), 2-1 Hirosawa, Wako 351-0198, Japan.
authors.forename: Yasunori
authors.initials: Y
authors.lastname: Tsuchiya
authors.forename: Yoshitaka
authors.initials: Y
authors.lastname: Hamashima
authors.forename: Mikiko
authors.initials: M
authors.lastname: Sodeoka
mesh_terms: D002384:Catalysis; D000431:Ethanol / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D014859:Warfarin / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007659:Ketones; D000431:Ethanol; D014859:Warfarin; D010165:Palladium