In situ generated Cr-complex [CrCl 2 (30 mol%), L7 (33 mol%) alkyl aldehyde 3 and redox-active ester 4 (Table ). The extensive electrochemical screening campaign outlined above uncovered an optimal combination of chromium (II) chloride as the chromium source (along with catalytic proton sponge to enhance complex formation), TDAE /TESCl as the additives, Al/Ni electrode materials, TBAClO4 electrolyte, and a high concentration (0.5M) in CH3CN. Of the chiral ligands explored, a unique sulfonamide-based structure (L7) 17 emerged as the optimum ligand. This final set of conditions provided a 51% isolated yield of benzylic alcohol 6 with 90% enantiomeric excess (Table ). Replacing CrCl2 with air-stable CrCl3 led to comparable yield but decreased enantio-selectivity (entry 1). The addition of TDAE significantly increased the reaction efficiency without impacting the enantioselectivity (entry 2). TESCl was found to be superior to Cp2ZrCl2 in terms of trapping the chromium alkoxides and regenerating the catalyst (entry 3). As for the electrochemical parameters, solvent choice was important wherein replacing CH3CN with DMF (entry 4) lead to diminished enantioselectivity, presumably due to undesired competing coordination. Constant voltage (entry 5), alternative anode (entry 6) or cathode (entry 7) materials as well as the identity of the electrolyte (entry 8) decreased the observed reaction yield. Notably, classic batch conditions with or without external reducing agents (entries 9 and 10) displayed far lower reactivity for this transformation.