title: Asymmetric hydrogenation of alpha-chloro aromatic ketones catalyzed by eta6-arene/TsDPEN-ruthenium(II) complexes.
abstract: Asymmetric hydrogenation of various alpha-chloro aromatic ketones with Ru(OTf)(TsDPEN)(eta6-arene) (TsDPEN = N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine) produces the chiral chlorohydrins in up to 98% ee. This reaction can be conducted even on a 206-g scale. The hydrogenation of an alpha-chloro ketone with a phenol moiety has been utilized for the synthesis of (R)-norphenylephrine without protection-deprotection operations. [reaction: see text].
authors.affiliation: Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan. ohkuma@eng.hokudai.ac.jp
authors.forename: Takeshi
authors.initials: T
authors.lastname: Ohkuma
authors.forename: Kunihiko
authors.initials: K
authors.lastname: Tsutsumi
authors.forename: Noriyuki
authors.initials: N
authors.lastname: Utsumi
authors.forename: Noriyoshi
authors.initials: N
authors.lastname: Arai
authors.forename: Ryoji
authors.initials: R
authors.lastname: Noyori
authors.forename: Kunihiko
authors.initials: K
authors.lastname: Murata
mesh_terms: D002384:Catalysis; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis* / Q000737:chemistry; D006865:Hydrogenation; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006841:Hydrocarbons, Aromatic; D007659:Ketones; D009942:Organometallic Compounds; D012428:Ruthenium