Preparation of Tertiary Amines by the Reaction of Iminium Ions Derived from Unsymmetrical Aminals with Zinc and Magnesium Organometallics

We report a convenient one-pot preparation of polyfunctional tertiary amines, including various biorelevant phenethylamines or ephedrine derivatives, via the reaction of new functionalized iminium ions with a variety of zinc and magnesium organometallic reagents. These iminium ions were generated from unsymmetrical aminals, obtained by the in situ addition of various amides to Tietze’s iminium salt [Me2NCH2 +CF3COO–]. A functionalized aniline, prepared by this method, was converted to a quinolidine via an intramolecular Heck reaction.