Direct electrochemical alpha-cyanation of N-protected cyclic amines

alpha-Cyanation of N-protected cyclic amines was achieved using a direct electrochemical method. Unsubstituted N-protected cyclic amines were easily cyanated at the alpha-position using an undivided cell in high yields; moreover, alpha-cyanation of alpha'-substituted pyrrolidine and alpha'-, beta'- or gamma-substituted piperidines smoothly proceeded in high yield and with high to excellent diastereoselectivity. alpha-Substituted N-cyano-pyrrolidines and -piperidines were also cyanated at the more substituted position (the alpha-position) using a divided cell with high yield and high regioselectivity.