Synthesis of chiral epichlorohydrin by chloroperoxidase-catalyzed epoxidation of 3-chloropropene in the presence of an ionic liquid as co-solvent

Asymmetric epoxidation of 3-chloropropene can be catalyzed by chloroperoxidase (CPO) from Caldariomyces fumago to prepare (R)-epichlorohydrin (ECH) in homogenous phosphate buffer/ionic liquid mixtures using r-butyl hydroperoxide (TBHP) as O-2 donor. Reaction conditions were optimized by the investigation of the choice of oxidants, the presence of ionic liquids (ILs), pH effect and CPO consumption. The best ECH yield reached 88.8% within a duration of 60 min with high enantiomeric excesses (e.e. 97.1%) at pH 5.5 and room temperature, using 1-ethyl-3-methylimidazolium [EMIM][Br] as co-solvent. The ILs with shorter carbon chain was more efficient on chiral ECH preparation. (C) 2010 Elsevier B.V. All rights reserved.