Racemic thiol esters of alpha-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/SnCl4. 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%.

Deracemization of thiol esters of a-arylpropionics acids

CLERICUZIO, Marco;DEGANI, Jacopo;DUGHERA, Stefano;FOCHI, Rita
2003-01-01

Abstract

Racemic thiol esters of alpha-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/SnCl4. 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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thiol esters of alpha-arylpropionic acids; enantioselective protonation; ibuprofen; naproxen
CLERICUZIO M; DEGANI I; S. DUGHERA; FOCHI R
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2318/4478
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