title: Enantioselective protonation of alkenyl trifluoroacetates catalyzed by chiral tin methoxide.
abstract: Go catalytic! A catalytic enantioselective protonation of alkenyl trifluoroacetates was achieved by using an in situ generated chiral tin bromide methoxide as the chiral catalyst in the presence of methanol. Optically active ketones containing a tertiary stereogenic center at the α-position were obtained with enantioselectivities of up to 94 % ee.
authors.affiliation: Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263-8522 (Japan), Fax: (+81) 43-290-2789. ayanagi@faculty.chiba-u.jp.
authors.forename: Akira
authors.initials: A
authors.lastname: Yanagisawa
authors.forename: Takuya
authors.initials: T
authors.lastname: Sugita
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Yoshida
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009947:Organotin Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014269:Trifluoroacetic Acid / Q000737:chemistry*
chemical_list: D000475:Alkenes; D006842:Hydrocarbons, Brominated; D007659:Ketones; D009947:Organotin Compounds; D014269:Trifluoroacetic Acid
keywords: alkenyl esters; asymmetric catalysis; ketones; protonation; tin