Highly diastereoselective synthesis of 2-substituted-1,3-diols catalyzed by ketoreductases

The stereoselective reduction of alpha-substituted-beta-hydroxy ketones for the preparation of the corresponding optically pure 2-monosubstituted or 2-disubstituted-1,3-diols is described. These transformations proceed in high optical purities and yields. Ketoreductases were able to catalyze the formation of either the syn or the anti diol, depending on the enzyme. By replacing the a-alkyl substituent for an OAc moiety, in low conversion time (<= 24 h), ketoreductases catalyzed the formation of the OAc-protected 1,2,3-triol, in high yield and with high optical purity (>99% de, >99% ee). This is a simple and highly stereoselective method for the synthesis of different diastereomers of chiral diols. (C) 2010 Elsevier Ltd. All rights reserved.