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

被引：24

作者：

Howard, James K. ^{[1
,2
]}

Mueller, Marion ^{[2
,3
]}

Berry, Alan ^{[2
,3
]}

Nelson, Adam ^{[1
,2
]}

机构：

[1] Univ Leeds, Sch Chem, Leeds LS2 9JT, W Yorkshire, England

[2] Univ Leeds, Astbury Ctr Struct Mol Biol, Leeds LS2 9JT, W Yorkshire, England

[3] Univ Leeds, Sch Mol & Cellular Biol, Leeds LS2 9JT, W Yorkshire, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 23期

关键词：

aldolase; asymmetric catalysis; chemoenzymatic synthesis; organofluorine compounds; ASYMMETRIC ALDOL REACTIONS; ENANTIOSELECTIVE SYNTHESIS; MECHANISTIC PROBES; FLUORINATION; CHEMISTRY; ALDEHYDES; ENZYMES;

D O I：

10.1002/anie.201602852

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The trans-o-hydroxybenzylidene pyruvate aldolasecatalysed 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 afluoro l3-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 Tvith potential value in drug discovery.

引用

页码：6767 / 6770

页数：4

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