Construction of diverse polycyclic N-heterocycles via cascade allylic amination/Diels-Alder reaction.

An efficient cascade approach for the construction of nitrogen-containing polycyclic compounds from amines tethered with an alkenyl (or alkynyl) group and divinyl carbonates is described. In the presence of Pd(0)-catalyst, an active zwitterionic allylpalladium species is generated and undergoes allylic amination with various amines followed by Diels-Alder reaction to form various polycyclic N -heterocyclic products, including hydrophenanthridines, hydrobenzo[ c ]azepines (hydro)isoindoles and hydrobenzo[ cd ]indoles.