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
收藏
页码：11063 / 11070
页数：8
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