Regioselective reactions of N-monosubstituted β-aminovinyl trifluoromethyl ketones with tosyl isocyanate

Abstract

The NH and α-CH insertion reactions of tosyl isocyanate with N-monosubstituted 4-amino-1,1,1-trifluorobut-3-en-2-ones have been studied. The regioselectivity of this reaction depends on the temperature, the nature of the solvent and the catalyst: high temperatures or basic catalysts direct in favour of NH insertion while low temperatures direct the process in favour of α-CH insertion.