Asymmetric syntheses of chiral propane-1,3-diols starting from malonic acid

Abstract

Syntheses of chiral intermediates having one tertiary asymmetric centre were carried out via chiral half-esters of monoalkylmalonic acids. The menthyl half-ester of ethylmalonic acid afforded a single diastereoisomer through crystallisation-induced asymmetric transformation (second-order asymmetric transformation). Furthermore enantioselective preparation of unsymmetrical propane-1,3-diol derivatives was achieved by the use of 8-phenylmenthyl half-esters.