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A Computational Study of the Stereoselective Decarboxylation in the Synthesis of Naproxen

✍ Scribed by Markus Drees; Lillian Kleiber; Martin Weimer; Thomas Strassner


Publisher
John Wiley and Sons
Year
2002
Tongue
English
Weight
124 KB
Volume
2002
Category
Article
ISSN
1434-193X

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✦ Synopsis


The antiinflammatory drug Naproxen has been synthesized via several enantioselective routes. The recently published synthesis involving the asymmetric decarboxylation of 2-cyano-2-(6-methoxy-naphth-2-yl)propionic acid (H. Brunner, P. Schmidt, Eur. J. Org. Chem. 2000, 2119) was investigated by quantum-chemical calculations. It was found that the stereochemistry of the products was determined by a concerted protonation/decarboxylation reaction.


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