Gem-difluorination of aminoalkynes via highly reactive dicationic species in superacid HF-SbF5: application to the efficient synthesis of difluorinated cinchona alkaloid …

…, H Carreyre, JP Gesson, MP Jouannetaud…

Index: Cantet, Anne-Celine; Carreyre, Helene; Gesson, Jean-Pierre; Jouannetaud, Marie-Paule; Renoux, Brigitte Journal of Organic Chemistry, 2008 , vol. 73, # 7 p. 2875 - 2878

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Citation Number: 15

Abstract

A variety of alkynylated amines, amides, and imides are reacted in the superacid system HF- SbF5 to give regioselectively new β-gem-difluoroamines. The reaction, which is not observed in pure HF, is consistent with the formation of a dicationic intermediate (ie, both vinylic and adjacent protonated N-ammonium cations). Application to the regioselective and efficient synthesis of difluorinated cinchona alkaloid derivatives is described.