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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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

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spelling	doaj-4df688a708814980bd8130a64cd25bc72020-11-25T02:00:18ZengSlovenian Chemical SocietyActa Chimica Slovenica1318-02071580-31552017-12-0164472773610.17344/acsi.2017.3543504Asymmetric Bio- and Chemoreduction of 2-Benzylidenecyclopentanone DerivativesBogdan Štefane0Uroš Grošelj1Jurij Svete2Franc Požgan3Faculty of Chemistry and Chemical Technology, University of LjubljanaFaculty of Chemistry and Chemical Technology, University of LjubljanaFaculty of Chemistry and Chemical Technology, University of LjubljanaFaculty of Chemistry and Chemical Technology, University of LjubljanaHighly 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.https://journals.matheo.si/index.php/ACSi/article/view/3543enantioselective reductioncyclopentanoneAKR1C inhibitorsoxazaborolidinebioreduction
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Bogdan Štefane Uroš Grošelj Jurij Svete Franc Požgan
spellingShingle	Bogdan Štefane Uroš Grošelj Jurij Svete Franc Požgan Asymmetric Bio- and Chemoreduction of 2-Benzylidenecyclopentanone Derivatives Acta Chimica Slovenica enantioselective reduction cyclopentanone AKR1C inhibitors oxazaborolidine bioreduction
author_facet	Bogdan Štefane Uroš Grošelj Jurij Svete Franc Požgan
author_sort	Bogdan Štefane
title	Asymmetric Bio- and Chemoreduction of 2-Benzylidenecyclopentanone Derivatives
title_short	Asymmetric Bio- and Chemoreduction of 2-Benzylidenecyclopentanone Derivatives
title_full	Asymmetric Bio- and Chemoreduction of 2-Benzylidenecyclopentanone Derivatives
title_fullStr	Asymmetric Bio- and Chemoreduction of 2-Benzylidenecyclopentanone Derivatives
title_full_unstemmed	Asymmetric Bio- and Chemoreduction of 2-Benzylidenecyclopentanone Derivatives
title_sort	asymmetric bio- and chemoreduction of 2-benzylidenecyclopentanone derivatives
publisher	Slovenian Chemical Society
series	Acta Chimica Slovenica
issn	1318-0207 1580-3155
publishDate	2017-12-01
description	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.
topic	enantioselective reduction cyclopentanone AKR1C inhibitors oxazaborolidine bioreduction
url	https://journals.matheo.si/index.php/ACSi/article/view/3543
work_keys_str_mv	AT bogdanstefane asymmetricbioandchemoreductionof2benzylidenecyclopentanonederivatives AT urosgroselj asymmetricbioandchemoreductionof2benzylidenecyclopentanonederivatives AT jurijsvete asymmetricbioandchemoreductionof2benzylidenecyclopentanonederivatives AT francpozgan asymmetricbioandchemoreductionof2benzylidenecyclopentanonederivatives
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Asymmetric Bio- and Chemoreduction of 2-Benzylidenecyclopentanone Derivatives

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