Issue 42, 2012
From the journal:

Chemical Communications

Stereoselective hydrofluorination of ynamides: a straightforward synthesis of novel α-fluoroenamides†

Guillaume Compain,a   Kevin Jouvin,b   Agnès Martin-Mingot,a   Gwilherm Evano,*bc   Jérome Marrotb  and  Sébastien Thibaudeau*a  

* Corresponding authors

a Superacid group in “Glycochimie, Superacide et Chimie des systèmes” team - Université de Poitiers, CNRS UMR 7285 IC2MP, 4, avenue Michel Brunet, F-86022 Poitiers Cedex, France
E-mail: sebastien.thibaudeau@univ-poitiers.fr
Fax: +33-549453501
Tel: +33-549454588

b Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles St-Quentin, 45 avenue des Etats Unis, 78035 Versailles Cedex, France

c Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université Libre de Bruxelles, Avenue F. D. Roosevelt 50, 1050 Brussels, Belgium

Abstract

α-Fluoroenamides, potent rigid fluorinated bioisosters of ureas, have been synthesized by a highly regio- and stereo-selective hydrofluorination of ynamides in anhydrous HF. This reaction provides the first general entry to α-fluoroenamides and can easily be applied to a wide range of substrates.

Graphical abstract: Stereoselective hydrofluorination of ynamides: a straightforward synthesis of novel α-fluoroenamides

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Article information

DOI
https://doi.org/10.1039/C2CC31768K
Article type
Communication
Submitted
09 Mar 2012
Accepted
23 Mar 2012
First published
26 Mar 2012

Chem. Commun., 2012,48, 5196-5198

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Stereoselective hydrofluorination of ynamides: a straightforward synthesis of novel α-fluoroenamides

G. Compain, K. Jouvin, A. Martin-Mingot, G. Evano, J. Marrot and S. Thibaudeau, Chem. Commun., 2012, 48, 5196 DOI: 10.1039/C2CC31768K

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