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Published on: August 12, 2019
Direct electrochemical alpha-cyanation of N-protected cyclic amines
Samuel Shikuku Libendi1, Yosuke Demizu, Osamu Onomura
1Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan.
Abstract:
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.
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