Cu(I)-Induced Activation of Furan for Inverse Electron Demand ADAR with Alkenes toward Regioselective Synthesis of Tetrahydropyridine

The aza-Diels-Alder reaction of various alkenes and in situ formed 1-aza-1,3-dienes from the reaction of furan/pyrrole/thiophene and PhINTs for the regioselective synthesis of tetrahydropyridine (THP) derivatives was realized. The reaction was catalyzed by Tp(Me2)Cu as a catalyst under very mild reaction conditions. Structurally different alkenes, along with an alkyne, have been utilized as dienophiles to afford a wide range of different THP derivatives up to 70% yield. The potential application of the envisaged method was also investigated by a gram-scale synthesis.