The lipase-catalyzed kinetic resolution of a series of aromatic β-hydroxy esters in organic media has been investigated. Decanoic acid and its esters were successfully used as acyl donors for selective O-acylation. The regio- and enantioselective enzymatic hydrolysis of the decanoate moiety of the diesters was also investigated. The effects of water, reaction temperature, and solvent type, and also the influence of substrates structure on the catalytic behavior of potential commercially available lipases were studied. A novel procedure was developed for the efficient and highly stereoselective synthesis of both enantiomers of both novel and known target compounds.