Journal
CATALYSIS SCIENCE & TECHNOLOGY
Volume 2, Issue 11, Pages 2200-2205Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2cy20329d
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Funding
- Toray Science Foundation
- Grants-in-Aid for Scientific Research [22350044] Funding Source: KAKEN
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An efficient protocol was developed to produce chiral 2-arylalkanoic esters in high yields (up to 99%) from racemic carboxylic acids utilizing the racetnization of the mixed-anhydrides generated from acid components with pivalic anhydride in the presence of an acyl-transfer catalyst The present DKR involves the enantio-discriminating esterification of the racemic 2-arylalkanoic acids and the rapid racemization of the chiral 2-arylalkanoic acids under suitable reaction conditions using pivalic anhydride, diisopropylethylamine, and benzo-tetramisole (BTM) in a polar solvent, and this method was successfully applied for the preparation of pharmacodynamically active (S)-enantiomers of nonsteroidal anti-inflammatory drugs (NSAIDs), such as ibuprofen and naproxen.
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