H. Brunner, P. Schmidt
2000
Citations
0
Influential Citations
4
Citations
Journal
Zeitschrift für Naturforschung B
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 (S)-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.