Howard, JK, Müller, M, Berry, A orcid.org/0000-0003-3502-0426 et al. (1 more author) (2016) An Enantio- and Diastereoselective Chemoenzymatic Synthesis of α-Fluoro β-Hydroxy Carboxylic Esters. Angewandte Chemie, 128 (23). pp. 6879-6882. ISSN 0044-8249
Abstract
The trans-o-hydroxybenzylidene pyruvate aldolase-catalysed reactions between fluoropyruvate and many (hetero)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.
Metadata
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-Non Commercial License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. |
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) |
Depositing User: | Symplectic Publications |
Date Deposited: | 16 Nov 2016 11:16 |
Last Modified: | 10 Apr 2019 14:19 |
Published Version: | https://doi.org/10.1002/ange.201602852 |
Status: | Published |
Publisher: | Wiley |
Identification Number: | 10.1002/ange.201602852 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:107478 |