Controllable enzymatic Markovnikov addition and acylation of thiols to vinyl esters

The chemical selectivity between Markovnikov addition and acylation in the reaction of thiols and vinyl esters were developed. The addition reaction was efficiently catalyzed by CAL-B at 50 degrees C in isopropyl ether, affording the Markovnikov adducts with good yields. Acylation was carried out under the catalysis Of D-amino acylase in DMF at 50 degrees C. A series of thioethers and thioesters were synthesized via the controllable enzymatic methods. (C) 2009 Elsevier B.V. All rights reserved.