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.
Libendi
Samuel Shikuku
SS
Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan.
Demizu
Yosuke
Y
Onomura
Osamu
O
D000588:Amines / Q000737:chemistry*; D003485:Cyanates / Q000737:chemistry*; D004563:Electrochemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010880:Piperidines / Q000737:chemistry; D011759:Pyrrolidines / Q000737:chemistry; D013237:Stereoisomerism
D000588:Amines; D003485:Cyanates; D010880:Piperidines; D011759:Pyrrolidines; C032727:piperidine