Enzyme-catalyzed enantioselective diaryl ketone reductions

Org Lett. 2007 Jan 18;9(2):335-8. doi: 10.1021/ol0627909.

Abstract

The synthesis of diarylmethanols via the reduction of a range of substituted benzophenone and benzoylpyridine derivatives with ketoreductase enzymes (KREDs) has afforded chiral products with high yield (>90%) and ee (up to >99%). Ortho, meta, and para substitutions with a variety of electron-donating, electron-withdrawing, and halogen groups were examined. Substitution at the ortho position and/or highly electronically dissymmetric molecules were not required for good selectivity, as is the case with conventional chemical catalyst reductions. [reaction: see text].

MeSH terms

  • Catalysis
  • Ketones / chemistry*
  • Methanol / analogs & derivatives*
  • Methanol / chemical synthesis*
  • Methanol / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Oxidoreductases / chemistry*
  • Stereoisomerism

Substances

  • Ketones
  • Oxidoreductases
  • Methanol