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Deracemization of thiol esters of α-arylpropionic acids

✍ Scribed by Marco Clericuzio; Iacopo Degani; Stefano Dughera; Rita Fochi

Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
216 KB
Volume
14
Category
Article
ISSN
0957-4166

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✦ Synopsis

Racemic thiol esters of a-arylpropionic acids were deracemized by a procedure which featured deprotonation with LDA or KHMDS, transformation into the TMS or TBDMS enol ethers, and enantioselective protonation of the silyl enol ethers using (R)-1,1%-bi-2-naphthol/SnCl 4 . Oxidative hydrolysis of the enantiomerically enriched mixtures of thiol esters thus obtained yielded the (S)-enantiomers of ibuprofen and naproxen with ees up to 82%.

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On the acidity of thiol esters
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Thiol eaters, important in the bioryntheeia of fatty acida, have been shown to be much more acidic than eaters(l). In order to rationalize the large difference in acidities, Cronyn and co-workers(2) proposed that the eater anion would be greatly destabilized relative to an a-keto carbanion because