We herein demonstrate the first successful application of chiral κ 2 -N,O-oxazolines as ligands in organometallic C-H activations, accomplishing an enantioselective cobaltaelectro-catalyzed annulation towards vicinal chiral C(sp 3 )-C(sp 3 ) bonds (Figure ). The significance of this ligand class is attributed to the ease of steric and electronic modification on the ligand's backbone through a modular synthetic route starting from commercially available precursors. Ligand parameterization through computationally guided feature analysis provided a detailed understanding of the steric and electronic descriptors of the preligands. This illustrates their potential for broad usage in enantioselective transition metal catalysis. Salient features of the current strategy are a) the formation of multiple C(sp 3 )-stereocenters, b) high diastereo-control of the newly formed C(sp 3 )-C(sp 3 ) bond, and c) the use of simple precursors and inexpensive cobalt catalyst. Our strategy renders diverse peripherally decorated biologically relevant chiral indanes consisting of an aliphatic azo moiety with multiple aliphatic carbon stereocenters (Figure ). The azo-functionality can be easily manipulated to valuable biologically relevant chiral amines.