α-Hydroxy ketones are important intermediates in various drugs and fine chemicals. Stereoselective synthesis of both symmetric and asymmetric compounds is demonstrated involving benzoin, 2–2’-furoin, phenylacetyl carbinol (PAC) and 2-hydroxy-1-phenylpropan-1-one (HPP) as representatives. Dynamic kinetic resolution of the racemic preparations was achieved in one-pot combining transesterification catalyzed by immobilized lipases from Pseudomonas stutzeri and Pseudozyma heterogeneous chemo-catalyst Zr-TUD-1 in water-free organic solvent. (S)-benzoin, (S)-2,2’-furoin, (S)-PAC and (R)-HPP were obtained with both high efficiency and high enantiomeric excess. Within 90 minutes, 2,45 g (S)-PAC butyrate (ee 88%) yielded from a 130 mL batch reaction demonstrating both technical feasibility and relevance for application.