Synthesis of Propargylamines via Michael Addition Using Methyl Vinyl Ketone Derivatives, 1-Alkynes, and Secondary Amines Catalyzed by Copper (I) Halides.

Propargylamines are synthesized from methyl vinyl ketone derivatives, 1-alkynes, and secondary amines catalyzed by Cu salts involving the Michael addition of amine followed by an unusual C-C bond cleavage and addition of metal acetylides formed in situ to iminium ions. In this approach, the di-, tri-, and tetrasubstituted propargylamines are synthesized in 46-98% yields.