Synthesis of Chiral Fluorinated Propargylamines via Chemoselective Biomimetic Hydrogenation.

A highly enantioselective synthesis of chiral fluorinated propargylamines was developed through phosphoric acid and ruthenium-catalyzed chemoselective biomimetic hydrogenation of the carbon-nitrogen double bond of fluorinated alkynyl ketimines in the presence of a carbon-carbon triple bond. This reaction features high chemoselectivity and slow background reaction. In addition, selective transformations of the chiral fluorinated propargylamines were also reported.