Brunner, Henri and Schmidt, Peter (2000) Asymmetric catalysis, 134. Naproxen derivatives by enantioselective decarboxylation. ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 55 (5). pp. 369-372. ISSN 0932-0776
Full text not available from this repository. (Request a copy)Abstract
2-Aryl-substituted propionic acids, such as the important anti-inflammatory agent Naproxen, exist in two enantiomeric forms. The S-enantiomer of 2- (6-methoxynaphth-2-yl)propionic acid 1 is about 28 times more effective than the (R)-enantiomer. A new catalytic method to synthesize Naproxen (S)-1 involves the enantioselective decarboxylation of suitably substituted malonic acid derivatives. Thus, 2-(6-methoxynaphth-2-yl) -2-methylmalonic acid 6 and its monoester 7 were stirred in THF with catalytic amounts of chiral bases, which induced decarboxylation. After work-up, optical inductions up to 39.8% ee were found in the resulting products 1 and 9. The optically active bases may be fully recycled by extraction.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | MALONIC-ACIDS; COPPER(I); naproxen; asymmetric catalysis; enantioselective decarboxylation; cinchona alkaloids |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Anorganische Chemie > Alumni or Retired Professors > Prof. Dr. Henri Brunner |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 17 May 2022 06:44 |
| Last Modified: | 17 May 2022 06:44 |
| URI: | https://pred.uni-regensburg.de/id/eprint/42559 |
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