Enantioselective electrocatalytic oxidation of racemic amines using a chiral 1-azaspiro[5.5]undecane N-oxyl radical

Abstract

A preparative electrocatalytic oxidation of racemic amines, which contain a chiral centre α to the amino group, on (6S, 7R, 10R)-4-acetylamino-2,2,7-trimethyl-10-isopropyl-1-azaspiro[5.5]undecane N-oxyl yielded mixtures of carbonyl compounds (54.3–66.1%) and amines (33.9–45.7%) after 5 h of electrolysis, in which the current efficiency, turnover number, enantiopurity of the remaining (R)-isomers and S values were 90.7–94.8%, 21.7–26.5, 62–78% and 4.7–5.8, respectively.