Asymmetric Bio- and Chemoreduction of 2-Benzylidenecyclopentanone Derivatives

Asymmetric Bio- and Chemoreduction of 2-Benzylidenecyclopentanone Derivatives

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...

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Bibliographic Details
Main Authors: Bogdan Štefane, Uroš Grošelj, Jurij Svete, Franc Požgan
Format: Article
Language:English
Published: Slovenian Chemical Society 2017-12-01
Series:Acta Chimica Slovenica
Subjects:
enantioselective reduction
cyclopentanone
AKR1C inhibitors
oxazaborolidine
bioreduction
Online Access:https://journals.matheo.si/index.php/ACSi/article/view/3543
Description
Summary: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.
ISSN:1318-0207
1580-3155

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