Molecules embracing a high fraction of chiral sp 3 carbon atoms (Fsp ) feature an increased rate of clinical success owing to their enhanced solubility, accessibility to more target space, and other pharmacological properties. As a consequence, enantioselective transition metal-catalyzed construction of Fsp -enriched molecules remained a dominant area of research in mainstream organic synthesis (Figure ). Conceptually, the enantioselective construction of Fsp 3 -enriched molecules generating multiple stereo-defined C(sp )-centers and quaternary chiral centers are among the most perplexing and fundamentally challenging formations in synthetic organic chemistry. Thus, assembling these moieties catalytically has been a cardinal objective for years. In this context, ligand-enabled enantioselective high-valent cobalt(III)-catalyzed C(sp )-H activations have evolved as a reliable platform to render chiral Fsp -enriched molecules from 2D chemical space. Chiral ligands play a critical role in these transformations determining the reactivity and selectivity. Thus, de novo design and structural modification of chiral ligands are integral parts of the advancement of this regime. Modular synthesis and on-demand tuning of the steric as well as electronic features of the ligands are the most sought-after attributes to maneuver reactivity and selectivity. Thus, dedicated efforts to quest for new ligand classes suitable for these reaction manifolds are necessary to identify new transformations. Thereafter, parametrization of the developed ligands with data-guided approaches can significantly reduce the number of required experiments for the ligand's successful modulations and provide an in-depth understanding of its structure-property relationships. Additionally, exploring the key interactions in intermediate states with a rational evaluation of the changing structural features strongly impacts the enantio-induction. It affords a predictive model to facilitate further upgrades and evolution of the ligand classes.