Stereoselective Synthesis of (Z)-beta-Enamido Triflates and Fluorosulfonates from N-Fluoroalkylated Triazoles
2019
Abstract
N-Fluoroalkylated 1,2,3-triazoles in the presence of triflic acid or fluorosulfonic acid underwent a cascade reaction consisting of triazole protonation, ring opening, nitrogen elimination, sulfonate addition, HF elimination, and hydrolysis to furnish novel trifluoromethanesulfonyloxy- or fluorosulfonyloxy-substituted enamides, respectively, in a highly stereoselective fashion. The vinyl triflates underwent cross-coupling reactions to a variety of substituted enamides and serve as sources of the aminovinyl cations.
In reactions with triflic acid, electron-rich triazoles afforded 2-fluoroalkylated oxazoles.