We initiated our studies by synthesizing a library of κ 2 -N,O-oxazoline-enolate (L1-L13) and κ 2 -N,O-oxazoline-amidate (L14-L22) preligands (see Supporting Information). We considered hydrazone 3a and olefin 4a as the model substrates for our study. Gratifyingly, the application of electro-oxidative conditions with graphite felt (GF) anode and Pt-cathode in ethanol medium combining Co(OAc)2•4H2O catalyst, preligand L1, and NaOPiv base delivered the desired product 5 in 72% yield, 84.5:15.5 e.r., and >20:1 d.r. (Scheme 1A). We continued our study by examining the library of synthesized preligands for the desired transformation (Scheme 1A). Systematic studies revealed that the enantioselectivity of the transformation is highly sensitive to the steric features of the ligand. Substitution in the enol backbone plays a crucial role in determining the enantioselectivity. The enantiomeric ratio (e.r.) drops significantly as the steric hindrance increases at the R 2 position (L2-L5). The presence of an electron-withdrawing group in the preligand backbone (L6) provided inferior results. Increasing the steric hindrance at R 3 (L7) further diminished the e.r. significantly. Next, the substitution pattern at the oxazoline moiety was examined (L9-L13), and the valinol-derived preligand (L12) performed particularly well, offering the highest e.r. of 97.5:2.5. Sterically hindered oxazoline-derived preligand L8 displayed reduced enantioselectivity. A similar trend was also observed for the κ 2 -N,O-oxazoline-amidate preligands (L14-L22), though reasonably poor yields were obtained in these cases. Noticeably, electron-deficient groups in the enol or amide motifs showcased detrimental effects ensuing poor yields of 5. Moreover, the observed ligands's tautomerism was shown to have no effect on the enantioinduction. Then, various common organic solvents were probed, and a mixture of ethanol and acetone served best among others (Scheme 1B, entries 1-4). Further experimentation with different carboxylate bases revealed NaOPiv as the optimal choice for this transformation (Scheme 1B, entries 5-7). It is worth noting that electrolysis of the reaction mixture was necessary to furnish high yields of the desired product (Scheme 1B, entry 8). No product was observed with L24 due to the ligand's steric hindrance, which obstructs the olefin coordination after hydrazone and ligand complexation. We further quantified the coordinating site accessibility using the percentage buried volume (%Vbur) at the cobalt. An exceedingly high %Vbur (87.1) was observed for L24 compared to the rest of the ligand set, which present %Vburs ranging from 70.4 to 76.1 (Scheme 1C).