title: Catalytic hydrogenation of alpha,beta-epoxy ketones to form beta-hydroxy ketones mediated by an NADH coenzyme model.
abstract: [reaction: see text] The hydrogenation of alpha,beta-epoxy ketones can be mediated by a catalytic amount of BNAH or BNA(+)Br(-) to form corresponding beta-hydroxy ketones in high yield. Na2S2O4 is used as the reducing agent to convert BNA(+)Br(-) to BNAH. A radical mechanism has been proposed to understand many observations of this catalytic reaction.
authors.affiliation: Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China.
authors.forename: Hua-Jian
authors.initials: HJ
authors.lastname: Xu
authors.forename: You-Cheng
authors.initials: YC
authors.lastname: Liu
authors.forename: Yao
authors.initials: Y
authors.lastname: Fu
authors.forename: Yun-Dong
authors.initials: YD
authors.lastname: Wu
mesh_terms: D002384:Catalysis; D003067:Coenzymes / Q000378:metabolism*; D006865:Hydrogenation; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D008954:Models, Biological; D015394:Molecular Structure; D009243:NAD / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013431:Sulfates / Q000737:chemistry
chemical_list: C445701:1-benzyl-1,4-dihydronicotinamide; D003067:Coenzymes; D007659:Ketones; D013431:Sulfates; D009243:NAD; C004850:sodium dithionate