Lewis-Acid-Catalyzed Direct Allylation of Electron-Poor N-Heterocyclic Amides through an Amide-Aldehyde-Alkene Condensation.

We report a general protocol for the direct N-allylation of electron-poor N-heterocyclic amides and sulfonamides via an amide-aldehyde-alkene condensation reaction catalyzed by a Lewis acid. This process has a broad substrate scope with respect to N-heterocyclic amides including carbamates, carboxamides, and N-methylsulfonamides, and provides efficient access to a variety of allylamine derivatives in good yield with high regioselectivity. The utility of this method was also demonstrated by the rapid synthesis of Naftifine from N-methyl-1-naphthamide, paraformaldehyde, and styrene in one-pot. [ABSTRACT FROM AUTHOR]