Enzyme-catalyzed enantioselective diaryl ketone reductions

Organic Letters
Matthew D TruppoPaul N Devine

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].

Citations

Apr 30, 2011·Chemical Reviews·Eduardo García-UrdialesVicente Gotor
Feb 1, 2008·Expert Opinion on Drug Discovery·Ramesh N Patel
Sep 18, 2015·Applied Microbiology and Biotechnology·Martina Letizia ContenteDiego Romano
May 8, 2015·Journal of the American Chemical Society·Taegyo LeeJohn F Hartwig
Sep 17, 2013·Chemistry & Biology·Pouya JavidpourShiou-Chuan Tsai
Jul 3, 2013·Journal of the American Chemical Society·Diego GhislieriNicholas J Turner
Aug 27, 2014·Chemistry : a European Journal·Samantha StanilandJonathan Clayden
Feb 28, 2008·Angewandte Chemie·Matthew D TruppoNicholas J Turner
Aug 30, 2019·Angewandte Chemie·Rick C BetoriKarl A Scheidt
Feb 16, 2020·Applied Microbiology and Biotechnology·Afifa Ayu KoesoemaTomoko Matsuda
Mar 27, 2020·ChemSusChem·Sachin HandaWilfried Braje
Nov 14, 2019·Applied Microbiology and Biotechnology·Afifa Ayu KoesoemaTomoko Matsuda
Feb 12, 2020·Communications Chemistry·Jacob E DanderNeil K Garg

Related Concepts

Sodium Methoxide
Catalysis
Ketones
Oxidation-Reduction
Oxidase
Molecular Stereochemistry

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