NAD(P)+-NAD(P)H MODEL .63. REGIOSELECTIVE REDUCTION OF DIENOIC KETONES AND ALDEHYDES WITH AN NAD(P)H MODEL ON SILICA-GEL

The Hantzsch ester reduces carbon-carbon double bonds in α,β-unsaturated ketones and aldehydes under the catalysis of silica gel. The 1,4-selectivity is satisfactorily high even in the reductions of polyenes conjugated to a carbonyl group. Methyl substituent at an olefinic position (α or β to the carbonyl group) retards the reduction. The reduction can be used as a useful tool in obtaining building blocks for the syntheses of terpenoids and their derivatives. © 1987 The Chemical Society of Japan.