Notably, enantioselective metallaelectro-catalyzed C-H activation has flourished as a resource-economic transformative tool for the sustainable synthesis of chiral organic molecules. Since our pioneering findings on enantioselective palladium, and 3d transition metal-catalyzed electro-oxidative C-H activation strategies, this realm has drawn significant attention from the synthetic community. Noteworthily, the advancement in 3d-metallaelectro-catalyzed C-H activations was mostly confined to 8-aminoquinoline directing group for C-H/N-H annulation reactions. The enantioselective construction of 5membered rings through a dicarbofunctionalization of olefins is rare. We have recently elucidated an enantioselective cobaltaelectro-catalyzed carboacylation of olefins, realized by an intramolecular addition/elimination process involving the electrophilic carbonyl moiety of the benzamide. These transformations essentially relied upon the formation of C(sp 2 )-C(sp 3 ) bonds and the migratory insertion onto the olefin governs the formation of stereogenic centers. Alternatively, aerobic cobalt-catalyzed C-H activation, first described by our group, was recently applied for a relevant enantioselective domino synthesis of bridged bicycles involving bridged bicyclic olefins. We envisioned adopting this pursuit for an enantioselective cobaltaelectro-catalyzed C-H activation engaging innate electrophilic hydrazone functionality as the directing group combining with olefins. We questioned whether novel κ 2 -N,O-oxazoline ligands could allow an enantioselective annulation following an elusive diastereoselective C(sp 3 )-C(sp 3 ) bond construction, accessing chiral Fsp 3 -rich molecules. Eventually, the addition of the C-Co bond of alleged intermediate B to the electrophilic C=N bond will govern the formation of a chiral azo compound (Figure ).