An Enantio‐ and Diastereoselective Chemoenzymatic Synthesis of α‐Fluoro β‐Hydroxy Carboxylic Esters |
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Authors: | Dr James K Howard Dr Marion Müller Prof Alan Berry Prof Adam Nelson |
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Institution: | 1. School of Chemistry and Astbury Centre for Structural Molecular Biology, University of Leeds, Leeds, UK;2. School of Molecular and Cellular Biology and Astbury Centre for Structural Molecular Biology, University of Leeds, Leeds, UK |
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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. |
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Keywords: | aldolase asymmetric catalysis chemoenzymatic synthesis organofluorine compounds |
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