Imino-ene reaction of N-tosyl arylaldimines with α-methylstyrene: application in the synthesis of important amines

Copper(II) or tin(II) trifluoromethanesulfonate in combination with TMSCl effectively activates a C-H bond for the imino-ene reaction of N-tosylarylaldimines with α-methylstyrene. A wide variety of N-tosylarylaldimines were used to give homoallylamines in good to excellent yields under mild conditions. The imino-ene adduct was converted into a β-amino ketone. The synthesis of a 2,4-substituted pyrrolidine and a piperidine was also achieved from the imino-ene product via a Mitsunobu reaction and a Grubbs cyclization, respectively.