Dynamic Kinetic Resolution of 2,3-Dihydrobenzo[b]furans: Chemoenzymatic Synthesis of Analgesic Agent BRL 37959

被引：10

作者：

Bongen, Patrick ^{[1
]}

Pietruszka, Joerg ^{[1
]}

Simon, Robert Christian ^{[1
]}

机构：

[1] Forschungszentrum Julich, Univ Dusseldorf, Inst Bioorgan Chem, D-52426 Julich, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2012年 / 18卷 / 35期

关键词：

chiral resolution; enantioselectivity; enzymes; hydrolases; dynamic kinetic resolution; ASYMMETRIC HYDROGENATION; ABSOLUTE-CONFIGURATION; CEPACIA LIPASE; RACEMIZATION; ACID; ENZYMES; COMBINATION; CATALYSTS; CD;

D O I：

10.1002/chem.201200683

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient asymmetric synthesis of (S)-2,3-dihydrobenzo[b]furan-3-carboxylic acid (8?a) and (S)-5-chloro-2,3-dihydrobenzo[b]furan-3-carboxylic acid (8?b) was established. Key to the success was the highly stereoselective enzymatic kinetic resolution of the corresponding methyl or ethyl esters that was further developed into a dynamic process. As a reliable and fast tool for analysing the enantiomeric excess, HPLC coupled with a CD detector was utilized. The route was completed by a FriedelCrafts acylation of ethyl (S)-5-chloro-2,3-dihydrobenzo[b]furan-3-carboxylate (7?c) followed by saponification leading to (S)-5-chloro-2,3-dihydrobenzo[b]furan-3-carboxylic acid (2), an analgesic agent.

引用

页码：11063 / 11070

页数：8

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