Metal-ammonia reduction and reductive alkylation of conjugated dienoic acids

Abstract

Conjugated dienoic acids are readily reduced or reductively alkylated with lithium-ammonia to their trans-β,γ-unsaturated and trans-α-alkyl- β,γ-unsaturated derivatives respectively. Competing protonation in the latter reaction detracts from its general use in synthesis; the origin of this side reaction is briefly discussed.