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An Enantio- and Diastereoselective Chemoenzymatic Synthesis of ?-Fluoro ?-Hydroxy Carboxylic Esters.

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 ?-fluoro ?-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.

SUBMITTER: Howard JK 

PROVIDER: S-EPMC5074308 | biostudies-literature | 2016 Jun

REPOSITORIES: biostudies-literature

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An Enantio- and Diastereoselective Chemoenzymatic Synthesis of α-Fluoro β-Hydroxy Carboxylic Esters.

Howard James K JK   Müller Marion M   Berry Alan A   Nelson Adam A  

Angewandte Chemie (International ed. in English) 20160419 23

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 fra  ...[more]

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