Efficient synthesis of α,β-unsaturated ketones with trans-selective Horner–Wadsworth–Emmons reaction in water

Abstract

Organic reactions in aqueous media are being developed because water is environmentally benign. The Horner–Wadsworth–Emmons reaction is a modified Wittig reaction for the synthesis of α,β-unsaturated ketones and other conjugated compounds. Here we prepared high molecular weight ketones by the Horner–Wadsworth–Emmons reaction of dimethyl-2-oxopropylphosphonate and various aldehydes in water at room temperature. The product was precipitated during the reaction process and was separated readily by a simple filtration in 90–99 % yield.