The ability of horse liver alcohol dehydrogenase (HLADH) to the enantioselective oxidation of primary–primary, primary–secondary and primary-tertiary aliphatic 1, 5-and 1, 6-diols 1a–i was studied. No enantioselectivity of the transformations of primary–primary 1, 6-diols 1a–d to ɛ-lactones 4a–d was observed. Regioselective oxidation of primary–secondary 1, 6-diols 1e, f and 1, 5-diols 1h, i afforded enantiomerically enriched ɛ-lactones 4e, f and δ- ...