In summary, we described an electrochemical cobalt-catalyzed C-H activation strategy for the challenging enantioselective formation of indoles featuring up to two different chiral C-N axes for the first time. The devised electrocatalysis is exceedingly mild and operational simple while generating only molecular hydrogen as the sole byproduct. Key to success was the development of a novel ligand system based on chiral κ 2 -N,O-oxazoline ureas for enantioselective transition metal catalysis. This was demonstrated by moderate to high yields and enantiomeric enrichment during catalysis. Using a linear regression model and DFT calculations, the key features from the ligand system in controlling selectivity and activity could be identified. An MLR model was developed to quantitatively demonstrate the key