title: Stereochemically controlled asymmetric 1,2-reduction of enones mediated by a chiral sulfoxide moiety and a lanthanum(III) ion.
abstract: Enantiomerically pure (Z)-β-sulfinyl allylic alcohols of either handedness can be readily prepared from (Z)-β-sulfinyl enones using NaBH(4) or DIBAL reductants in the presence of LaCl(3) as a chelating agent. A chiral sulfoxide auxiliary induces the remote 1,2-asymmetric reduction (1,4-induction) to afford various chiral allylic alcohols in high yields with excellent stereoselectivities (up to 100% de).
authors.affiliation: School of Pharmacy, Nihon University, 7-7-1 Narashinodai, Funabashi-shi, Chiba, 274-8555, Japan.
authors.forename: Shigeyasu
authors.initials: S
authors.lastname: Motohashi
authors.forename: Kouichi
authors.initials: K
authors.lastname: Nagase
authors.forename: Toshinori
authors.initials: T
authors.lastname: Nakakita
authors.forename: Takeshi
authors.initials: T
authors.lastname: Matsuo
authors.forename: Yoshikazu
authors.initials: Y
authors.lastname: Yoshida
authors.forename: Takashi
authors.initials: T
authors.lastname: Kawakubo
authors.forename: Motofumi
authors.initials: M
authors.lastname: Miura
authors.forename: Masaharu
authors.initials: M
authors.lastname: Toriyama
authors.forename: Mikhail V
authors.initials: MV
authors.lastname: Barybin
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D007811:Lanthanum / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D020005:Propanols / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D013454:Sulfoxides / Q000737:chemistry*
chemical_list: D000475:Alkenes; D007659:Ketones; D009942:Organometallic Compounds; D020005:Propanols; D013454:Sulfoxides; C006463:allyl alcohol; D007811:Lanthanum