Optically active cis-1,3-cyclohexanedicarboxylic acid monoesters with high enantiomeric purity and process for their preparation

摘要

Optically active cis-1,3-cyclohexanedicarboxylic acid monoesters of 90% enantiomeric excess (ee) and methods of preparing the monoesters are described. One method contacts a cis-1,3-cyclohexanedicarboxylic acid diester with a lipase under aqueous conditions to enantioselectively produce the optically active cis-1,3-cyclohexanedicarboxylic acid monoester. Another method reacts a mixture of cis- and trans-1,3-cyclohexanedicarboxylic acids under conditions sufficient to form a cis-cyclic anhydride, esterifies the cis-cyclic anhydride to produce a cis-1,3-cyclohexanedicarboxylic acid diester and then contacts under aqueous conditions the diester with a lipase to enantioselectively produce the optically active cis-1,3-cyclohexanedicarboxylic acid monoester.