Deracemization of thiol esters of alpha-arylpropionic acids

Marco CLERICUZIO, I DEGANI, S DUGHERA, R. FOCHI

Risultato della ricerca: Contributo su rivistaArticolo in rivistapeer review

Abstract

Racemic thiol esters of α-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%.

Lingua originaleInglese
pagine (da-a)119-125
Numero di pagine7
RivistaTETRAHEDRON-ASYMMETRY
Volume14
Stato di pubblicazionePubblicato - 2003

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