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Dynamic Kinetic Resolution of 2,3-Dihydrobenzo[b]furans: Chemoenzymatic Synthesis of Analgesic Agent BRL 37959.
MedLine Citation:
PMID:  22829350     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
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 Friedel-Crafts 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.
Authors:
Patrick Bongen; Jörg Pietruszka; Robert Christian Simon
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-7-24
Journal Detail:
Title:  Chemistry (Weinheim an der Bergstrasse, Germany)     Volume:  -     ISSN:  1521-3765     ISO Abbreviation:  -     Publication Date:  2012 Jul 
Date Detail:
Created Date:  2012-7-25     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9513783     Medline TA:  Chemistry     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Affiliation:
Institut für Bioorganische Chemie der Heinrich-Heine Universität Düsseldorf im Forschungszentrum Jülich, Stetternicher Forst, Geb. 15.8, 52426 Jülich (Germany), Fax: (+49) 2461-616196.
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