Moreover, the enantioselective formation of the chiral C-N axis was centered on the directing group. In contrast, easily accessible 1-alkynyl indoles were used in atropo-enantioselective C-H/N-H annulations with chiral rhodium catalysts furnishing valuable indoles with one chiral C-N axis in a single step (Scheme 1A). However, chiral precious metal catalysts acquired from a multi-step synthesis sequence proved necessary to achieve high enantioselectivities. Despite these advances, the enantioselective C-H/N-H annulation of 1-alkynyl indoles by earth-abundant cobalt electrocatalysis remains elusive. Early preliminary findings by Andersson and Notash introduced chiral κ 2 -N,O-oxazoline enolates and amides as ligands for 3d transition metals. To the best of our knowledge the application of these types of ligands to enantioselective transition metal catalysis is scarce and only one example was reported thus far. Therefore, we questioned the suitability of these ligands and our developed multivariate linear regression (MVLR) model to accomplish challenging atropo-enantioselective C-H/N-H annulations with 1-alkynyl indoles (Scheme 1B). As a result, we, herein, we describe the successful development of this strategy including the discovery of novel chiral oxazoline urea preligands (UL). Hence, we show their use in challenging multiple atropo-enantioselective C-H/N-H annulations with 1-alkynyl indoles furnishing atropoisomers with up to two C-N chiral axes that are potentially attractive for pharmaceuticals, agrochemicals, and chiral ligands (Scheme 1C). Salient features of our cobalt electrocatalysis include 1) a double enantioselective C-H activation strategy furnishing atropoisomers with dual chiral C-N axial chirality, 2) the discovery of novel oxazoline urea and thiourea preligands, 3) cobalt as an earth-abundant 3d transition metal catalyst, 4) electrocatalysis with molecular hydrogen as the sole byproduct, and 5) high enantio-and diastereoselectivities (up to 99.5:0.5 e.r., >20:1 d.r.).