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The studies on the chemoenzymatic synthesis of 2-benzyl-3-butenoic acid
Catalysis Communications ( IF 3.4 ) Pub Date : 2018-05-29 , DOI: 10.1016/j.catcom.2018.05.020
Filip Borys , Daniel Paprocki , Dominik Koszelewski , Ryszard Ostaszewski

The studies on the chemoenzymatic synthesis of 2-benzyl-3-butenoic acid 3 were performed. The alkylation of dienolates derived from the crotonic and vinylacetic acids with different types of alkylating agents was examined. In all cases the inseparable mixture of isomeric acids 3 and 4 were obtained. Chemoselective enzymatic esterification of those mixtures provides ester 6 in 86% yield as a single product without double bond isomerization. None common method can be used for its hydrolysis since under basic conditions only isomeric acid 5 is formed. To overcome this limitation enzyme catalysed hydrolysis process was design. This protocol afforded isomerically pure acid 3 in 98% yield.



中文翻译:

化学合成2-苄基-3-丁烯酸的研究

化学合成2-苄基-3-丁烯酸3的研究。检查了来自巴豆酸和乙烯基乙酸的二烯酸酯与不同类型的烷基化剂的烷基化。在所有情况下,均获得了异构体3和4的不可分离的混合物。这些混合物的化学选择性酶促酯化以单一产物形式提供酯6,收率为86%,而没有双键异构化。没有一种通用的方法可用于其水解,因为在碱性条件下仅形成异构酸5。为了克服该限制,设计了酶催化的水解过程。该方案以98%的产率提供了异​​构纯的酸3。

更新日期:2018-05-29
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