Enzyme-catalyzed enantioselective diaryl ketone reductions.
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].
Truppo
Matthew D
MD
Department of Process Research, Merck Research Laboratories, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, USA. matthew_truppo@merck.com
Pollard
David
D
Devine
Paul
P
D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D000432:Methanol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010088:Oxidoreductases / Q000737:chemistry*; D013237:Stereoisomerism
D007659:Ketones; D010088:Oxidoreductases; D000432:Methanol