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

Full Text: HTML

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. ...

Related Articles:

The Identification of the Amino Acids: p-Toluenesulfonyl1 Chloride as a Reagent

[McChesney; Swann Journal of the American Chemical Society, 1937 , vol. 59, p. 1116]

Preparation of both enantiomers of 1-allyl-1, 2, 3, 4-tetrahydro-β-carboline using allyltin reagents and a chiral auxiliary derived from l-proline

[Itoh, Takashi; Matsuya, Yuji; Enomoto, Yasuko; Ohsawa, Akio Tetrahedron, 2001 , vol. 57, # 34 p. 7277 - 7289]

Preparation of both enantiomers of 1-allyl-1, 2, 3, 4-tetrahydro-β-carboline using allyltin reagents and a chiral auxiliary derived from l-proline

[Itoh, Takashi; Matsuya, Yuji; Enomoto, Yasuko; Ohsawa, Akio Tetrahedron, 2001 , vol. 57, # 34 p. 7277 - 7289]

Stereoselective aldol condensations via boron enolates

[Evans,D.A.; Nelson,J.V.; Vogel,E. Journal of the American Chemical Society, 1981 , vol. 103, p. 3099]

More Articles...