Literature DB >> 17217298

Enzyme-catalyzed enantioselective diaryl ketone reductions.

Matthew D Truppo1, David Pollard, Paul 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].

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Year:  2007        PMID: 17217298     DOI: 10.1021/ol0627909

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  8 in total

1.  Spiroborate esters in the borane-mediated asymmetric synthesis of pyridyl and related heterocyclic alcohols.

Authors:  Viatcheslav Stepanenko; Melvin De Jesús; Wildeliz Correa; Irisbel Guzmán; Cindybeth Vázquez; Lymaris Ortiz; Margarita Ortiz-Marciales
Journal:  Tetrahedron Asymmetry       Date:  2007-11-26

2.  Combined Photoredox/Enzymatic C-H Benzylic Hydroxylations.

Authors:  Rick C Betori; Catherine M May; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-26       Impact factor: 15.336

3.  Rhodium-catalyzed enantioselective silylation of arene C-H bonds: desymmetrization of diarylmethanols.

Authors:  Taegyo Lee; Tyler W Wilson; Robert Berg; Per Ryberg; John F Hartwig
Journal:  J Am Chem Soc       Date:  2015-05-20       Impact factor: 15.419

4.  Structural and biochemical analyses of regio- and stereospecificities observed in a type II polyketide ketoreductase.

Authors:  Pouya Javidpour; Tyler Paz Korman; Gaurav Shakya; Shiou-Chuan Tsai
Journal:  Biochemistry       Date:  2011-05-04       Impact factor: 3.162

5.  Enantioselective Copper(I)-Catalyzed Alkynylation of Oxocarbenium Ions to Set Diaryl Tetrasubstituted Stereocenters.

Authors:  Srimoyee Dasgupta; Thomas Rivas; Mary P Watson
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-25       Impact factor: 15.336

6.  The determinants of activity and specificity in actinorhodin type II polyketide ketoreductase.

Authors:  Pouya Javidpour; Joel Bruegger; Supawadee Srithahan; Tyler P Korman; Matthew P Crump; John Crosby; Michael D Burkart; Shiou-Chuan Tsai
Journal:  Chem Biol       Date:  2013-09-12

7.  Enzymatic desymmetrising redox reactions for the asymmetric synthesis of biaryl atropisomers.

Authors:  Samantha Staniland; Bo Yuan; Nelson Giménez-Agulló; Tommaso Marcelli; Simon C Willies; Damian M Grainger; Nicholas J Turner; Jonathan Clayden
Journal:  Chemistry       Date:  2014-08-22       Impact factor: 5.236

8.  Chemoenzymatic conversion of amides to enantioenriched alcohols in aqueous medium.

Authors:  Jacob E Dander; Maude Giroud; Sophie Racine; Evan R Darzi; Oscar Alvizo; David Entwistle; Neil K Garg
Journal:  Commun Chem       Date:  2019-07-19
  8 in total

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