TBAF-promoted carbanion-mediated sulfonamide cyclization of CF₃-substitutedN-allenamides: an access to fluorinated γ-sultams

Abstract

Upon treatment with TBAF, CF3-substituted N-allenamides were transformed into γ-sultams. Cyclic sulfonamides bearing an ene-gem-difluorinated tether could be obtained by addition of acetic acid to the ammonium salt whereas TBAF...

Metal free regio – and stereoselective semireduction of CF3-substituted N-allenamides

“…Allenamides represent a privileged subclass of allenes and have become key substrates in myriad transformations, 1 including those leading to the construction of nitrogen-containing scaffolds. 2 Regioselective semireduction of N -allenamides paves the way for the synthesis of both enamides and allylic amides, two ubiquitous classes of synthetic intermediates critical for the synthesis of heterocyclic compounds. Enamides and allylic amides represent bioactive pharmacophores in drug molecules and have become more popular reagents for the incorporation of nitrogen-based functional groups.…”