Abstract: In an effort to develop new ways of synthesizing polycyclic alkaloids, we successfully added silyl enol ethers, allylsilanes, and enamines to
iminium ions generated from amides. Because of their higher oxidation state, such iminiums show a yet unexploited advantage of potential
double cyclizations over standard Mannich monocyclizations. We report herein the first example of tethered nonaromatic carbon nucleophiles
adding to activated amides for the generation of enaminals of various ring sizes, with endo- or exo-cyclic nitrogen.