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Keywords:

  • alcohols;
  • biocatalysis;
  • enantioselectivity;
  • enzymes;
  • kinetic resolution

Abstract

The enantioselective oxidation of (1R,2S)-1-phenyl-1,2-propanediol [(1R,2S)-1], mediated by baker’s yeast, gave (−)-(S)-1-phenyl-2-hydroxy-1-propanone [(S)-2] in 64 % isolated yield and 93 % ee. Kinetic experiments of the bio-oxidation of (±)-anti-1 revealed that the enantiomer (1R,2S)-1 was more reactive than (1S,2R)-1. Therefore, this result allowed us to devise a kinetic resolution experiment to obtain (1S,2R)-1 in >99 % ee from (±)-anti-1. The preparation of (1S,2R)-1 is interesting, as it is the antipode of the product obtained by the reduction of 1-phenyl-1,2-propanedione using baker’s yeast. Other microorganisms, such as Micrococcus luteus, Candida albicans, and Geotrichum candidum, were also used for kinetic resolution experiments of (±)-anti-1. The best result was obtained using Geotrichum candidum, which gave (1S,2R)-1 in 32 % yield and 99 % ee.