Organic & biomolecular chemistry

Oxidative desulfurization–fluorination of thioethers. Application for the synthesis of fluorinated nitrogen containing building blocks

V Hugenberg, R Fröhlich, G Haufe

Index: Hugenberg, Verena; Froehlich, Roland; Haufe, Guenter Organic and Biomolecular Chemistry, 2010 , vol. 8, # 24 p. 5682 - 5691

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Citation Number: 8

Abstract

An oxidative desulfurization–fluorination protocol has been used to synthesize (2S)-2- (difluoromethyl)-N-tosylpyrrolidine (6a) and (2S)-2-(trifluoromethyl)-N-tosylpyrrolidine (7a) from the (2S)-prolinol-derived (2S)-2-(4-chlorophenylthiomethyl)-N-tosylpyrrolidine (9) or (2S)-2-(dithian-2-yl)-N-tosylpyrrolidine (5). Efforts to prepare 3, 3-difluoroalanine similarly from an N-protected S-aryl-cysteine ester 17 gave only traces of the target compound 18. ...