Reduction of alpha,beta unsaturated carbonyl compounds by Ni2+-BH4-

The reduction of alpha,beta unsaturated carbonyl compounds by sodiumborohyd ride is catalysed by Ni(bpy)Cl-2 (bpy = 2,2'-bipyridine). Various carbonyl compounds having the general formula RtCH=CHCRO [where R-1, R = C6H5, H; p- MeO-C6H4-,C6H4; p-CH3-C6H4, C6H5; (m-OMe-)(p-OMe-)C6K2, C6H5; C6H5, (CH3)(2 )CH-; CH3, H; m-Br-C6H4-, C6H5] are reduced to corresponding allylicalcohol [R1CH=CHCRHOH] at 25 degreesC within half an hour. During these reductions the double bond is partially reduced to give saturated alcohols as minor p roducts having the molecular formula R1CH2CH2CRHOH. The reduction of trans- 3-phenyl-2-propenal with NaBH4 and catalytic amounts of Ni(bpy)Cl-2 in solv ents containing active deuterium (D2O, CD3OD), leads to the partial incorpo ration of deuterium at the alpha and gamma positions to give C-D bonded alc ohols. (C) 2001 Elsevier Science B.V. All rights reserved.