INFLUENCE OF STRUCTURAL FACTORS AND ENZYME TYPE ON THE REACTIVITY AND ENANTIOSELECTIVITY OF THE ENZYMATIC ESTERIFICATION OF BICYCLIC MESO DIALCOHOLS

The meso dialcohols 1 - 7 obtained from the Diels-Alder adducts furan/maleic anhydride, furan/dimethyl acetylenedicarboxylate, and cyclopentadiene/maleic anhydride, were subjected to enzymatic esterification in organic solvents. A mixture of the corresponding chiral monoacetates and the meso diacetates was obtained. It has been found that reaction rate and enantioselectivity markedly depend on substrate structure, temperature, enzyme type, and nature of the solvent. The presence of an oxygen bridge and an exo configuration are the tow structural features which lead to the highest enantioselectivity values.