Catalytic hydrogenation of alpha,beta-epoxy ketones to form beta-hydroxy ketones mediated by an NADH coenzyme model.
[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.
Xu
Hua-Jian
HJ
Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China.
Liu
You-Cheng
YC
Fu
Yao
Y
Wu
Yun-Dong
YD
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
C445701:1-benzyl-1,4-dihydronicotinamide; D003067:Coenzymes; D007659:Ketones; D013431:Sulfates; D009243:NAD; C004850:sodium dithionate