title: Asymmetric hydrogenation of alkynyl ketones with the η(6)-arene/TsDPEN-ruthenium(II) catalyst.
abstract: Enantioselective hydrogenation of alkynyl ketones catalyzed by Ru(OTf)(TsDPEN)(η(6)-p-cymene) (TsDPEN = N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine) affords the propargylic alcohols in up to 97% ee. The alkynyl moieties are left intact in most cases. The reaction can be conducted with a substrate-to-catalyst molar ratio as high as 5000 under 10 atm of H2. The mode of enantioselection is elucidated with the transition state models directed by the CH/π attractive interaction between the substrate and the catalytic species.
authors.affiliation: Division of Chemical Process Engineering and Frontier Chemistry Center, Faculty of Engineering, Hokkaido University , Sapporo, Hokkaido 060-8628, Japan, and Central Research Laboratory, Technology and Development Division, Kanto Chemical Co., Inc. , Soka, Saitama 340-0003, Japan.
authors.forename: Noriyoshi
authors.initials: N
authors.lastname: Arai
authors.forename: Hironori
authors.initials: H
authors.lastname: Satoh
authors.forename: Noriyuki
authors.initials: N
authors.lastname: Utsumi
authors.forename: Kunihiko
authors.initials: K
authors.lastname: Murata
authors.forename: Kunihiko
authors.initials: K
authors.lastname: Tsutsumi
authors.forename: Takeshi
authors.initials: T
authors.lastname: Ohkuma