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 ALFA-ARYLPROPIONIC 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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