Howard, JK, Muller, M, Berry, A et al. (1 more author) (2016) An enantio- and diastereoselective chemoenzymatic synthesis of α-fluoro β-hydroxy carboxylic esters. Angewandte Chemie International Edition, 55 (23). pp. 6767-6770. ISSN 1433-7851
Abstract
The trans-o-hydroxybenzylidene pyruvate aldolase-catalysed reactions between fluoropyruvate and many (het)aromatic aldehydes yield aldol adducts without subsequent dehydration. Treatment of the reaction products with hydrogen peroxide yields the corresponding syn-configured α-fluoro β-hydroxy carboxylic acids which have >98% ee. The overall chemoenzymatic approach, in which fluoropyruvate serves as a fluoroacetate equivalent, may be exploited in the synthesis of polar building blocks and fragments with potential value in drug discovery.
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Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution-NonCommercial License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. |
Keywords: | chemoenzymatic synthesis; aldolase; organofluorine compounds; asymmetric catalysis |
Dates: |
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Institution: | The University of Leeds |
Academic Units: | The University of Leeds > Faculty of Biological Sciences (Leeds) > School of Molecular and Cellular Biology (Leeds) The University of Leeds > Faculty of Engineering & Physical Sciences (Leeds) > School of Chemistry (Leeds) > Organic Chemistry (Leeds) |
Depositing User: | Symplectic Publications |
Date Deposited: | 11 Apr 2016 15:57 |
Last Modified: | 10 Apr 2019 14:18 |
Published Version: | https://dx.doi.org/10.1002/anie.201602852 |
Status: | Published |
Publisher: | Wiley |
Identification Number: | 10.1002/anie.201602852 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:98011 |
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