Enantioselective acylation catalyzed by the thioamide modified 1-methylhistidine methyl ester 1 in combination with DABCO-mediated racemization of the substrate led to the efficient dynamic kinetic resolution of meso-1,2-diol monodichloroacetates. In this way, cyclic and acyclic meso-1,2-diol monodichloroacetates can be transformed to the enantiomerically enriched (1S,2R)-heterosubstituted diol diesters which are stable in enantiomerically pure form and can be readily used for further organic transformations.