Rapid Generation of Tetrahydropyridines and Tetrahydroquinolines by Dearomative Cyanation/Grignard Addition.

A rapid, practical and scalable method for the reductant and tansition-metal-free synthesis of a variety of novel 2,4-disubstituted tetrahydropyridines and tetrahydroquinolines is disclosed. The method is based upon dearomative functionalization of pyridines or quinolines to generate amino nitrile intermediates as masked iminium ions, which then react rapidly with various Grignard reagents in complete stereocontrol.