Asymmetric Bio- and Chemoreduction of 2-Benzylidenecyclopentanone Derivatives

Bogdan Štefane, Uroš Grošelj, Jurij Svete, Franc Požgan

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.

Keywords


enantioselective reduction; cyclopentanone; AKR1C inhibitors; oxazaborolidine; bioreduction

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DOI: http://dx.doi.org/10.17344/acsi.2017.3543

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