Asymmetric Bio- and Chemoreduction of 2-Benzylidenecyclopentanone Derivatives

Authors

  • Bogdan Štefane Faculty of Chemistry and Chemical Technology, University of Ljubljana
  • Uroš Grošelj Faculty of Chemistry and Chemical Technology, University of Ljubljana
  • Jurij Svete Faculty of Chemistry and Chemical Technology, University of Ljubljana
  • Franc Požgan Faculty of Chemistry and Chemical Technology, University of Ljubljana

DOI:

https://doi.org/10.17344/acsi.2017.3543

Keywords:

enantioselective reduction, cyclopentanone, AKR1C inhibitors, oxazaborolidine, bioreduction

Abstract

Highly efficient asymmetric reduction of 2-benzylidenecyclopentanone derivatives to give selectively the exocyclic allylic alcohols in ee's up to 96% was performed with chiral oxazaborolidine-based catalysts. Complete enantioselectivity furnishing (S)-configured alcohol product can be achieved by bioreduction of 2-(4-chlorobenzylidene)cyclopentanone with Daucus carota root. The synthesized compounds can serve as enantiomerically enriched standards for the monitoring of the enzyme-catalyzed redox processes.

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Published

12.12.2017

Issue

Vol. 64 No. 4 (2017): Acsi

Section

Organic chemistry

License

Except where otherwise noted, articles in this journal are published under the Creative Commons Attribution 4.0 International License