Remarkably selective reduction of the α,β-Carbon-Carbon double bond in highly activated α,β,γ,δ-unsaturated alkenes by the InCl3-NaBH4 reagent system

A combination of sodium borohydride and a catalytic amount of indium(III) chloride in acetonitrile reduces exclusively the alpha,beta-carbon-carbon double bond in alpha,beta,gamma,delta-unsaturated diaryl ketones, dicarboxylic ester, cyano-ester, and dicyano compounds.