PREPARATION OF OPTICALLY ACTIVE THIOESTER AND OPTICALLY ACTIVE THIOL WHICH IS DERIVATIVE THEREOF

摘要

PURPOSE:To prepare an optically active thioester, in high yield, rather easily, by the radical addition reaction of thioacetic acid and an olefin compound in the presence of a specific optically active compound. CONSTITUTION:An optically active thioester is prepared by the radical addition reaction of thioacetic acid and an olefin compound in the presence of an optically active alcohol or carboxylic acid of formula (R1-3 are H, alkyl, phenyl, etc.; X is OH or carboxyl). Reduction of the thioester affords its derivative, an optically active thiol. Since the optically active ester obtained is alpha- or beta-addition compound according to the stability of the radical reaction, the reaction proceeds through a diastereomer-type intermediate with enantiometric differentiation. The optically active alcohol is, e.g. menthol, and the optically active carboxylic acid is, e.g. deoxycholic acid.