Kinetic Resolution of Chiral α-Hydroperoxy Esters by Horseradish Peroxidase-Catalyzed Enantioselective Reduction to α-Hydroxy Esters

Article abstract of DOI:10.1016/0957-4166(95)00121-5

The kinetic resolution of the methyl α-hydroperoxy esters 4 has been investigated by horseradish peroxidase (HRP)-catalyzed reduction to the corresponding optically active α-hydroxy esters 5 in the presence of guaiacol.The method allows for the first time the preparation of enantiomerically pure (ee>97percent) methyl (R)-2-hydroperoxybutyrate (4a).The HRP enzyme is sensitive to the steric demand of the ester alkyl side chain, as manifested by ethyl (ee>97percent) and isopropyl (ee 79percent), while the tert-butyl derivative is not accepted by the enzyme (no reduction).