In summary, we have devised an enantioselective cobaltaelectro-catalyzed annulation between aryl hydrazones and olefins, constructing chiral Fsp 3 -rich indanes. The current method is mild, operationally simple, and scalable. A notable feature of the present strategy is the highly enantioand diastereo-selective C(sp 3 )-C(sp 3 ) bond formation. Simultaneously, the untapped potential of chiral κ 2 -N,O-oxazoline preligands was exploited for an enantioselective C-H activation strategy. This preligand class allows for modular stereo-electronic modifications, offering beneficial features for asymmetric transition metal catalysis in general. DFT feature-based multivariate regression modeling disclosed a suitable MVLR model describing the ligand's modularity towards diverse electronic, steric, and interaction behavior influencing the enantioselectivity. Furthermore, the univariate classification unveiled the role on interaction energy and NBO charge influencing the reaction yield. The in-depth analysis and the generated model can facilitate the rational design and efficient screening of novel κ 2 -N,O-oxazoline preligands, extending its applicability towards other asymmetric transformations. We anticipate that our findings provide a valuable platform for chiral ligands and expect their usage in asymmetric transition metal catalysis in the future.