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

G. Compain (1) , K. Jouvin (2) , A. Martin-Mingot (1) , G. Evano (2, 3) , J. Marrot (2) , S. Thibaudeau (1)

1 Chimie de l'eau et traitement de l'eau
2 ILV - Institut Lavoisier de Versailles
3 Univ Libre Brussels, Serv Chim & Phys Chim Organ, Lab Chim Organ, B-1050 Brussels, Belgium

alpha-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 alpha-fluoroenamides and can easily be applied to a wide range of substrates.

Domaines: Catalyse; Chimie organique; Autre

G. Compain, K. Jouvin, A. Martin-Mingot, G. Evano, J. Marrot, et al.. Stereoselective hydrofluorination of ynamides: a straightforward synthesis of novel alpha-fluoroenamides. Chemical Communications, 2012, 48 (42), pp.5196-5198. ⟨10.1039/c2cc31768k⟩. ⟨hal-00834286⟩