Synthesis of new trifluoromethyl peptidomimetics with a triazole moiety

gem-Chloroamine CF3CH(Cl)NHAc 1 reacts in a one-pot sequence with NaN3 to afford trifluoromethyl azido compound 2 and further undergoes a Huisgen 1,3-dipolar cycloaddition with alkynes to yield 1,4-disubstitued 1,2,3-triazoles. The reaction is catalyzed by Cu(II) species (Cu(OAc)2, 10 mol %) without any reducing agent, and the corresponding products are afforded in high yields (74–87%). This process offers thus an entry to new trifluoromethyl pseudopeptides.