The development of optimized conditions for this unique electrochemical oxidative cyclization warrants further comment. Initial electrolysis of 14 to electrolysis in methanol or HFIP resulted in benzylic solvent trapping, alongside trace 15 in the latter case. Nevertheless, the clean benzylic oxidation was encouraging, and after screening a series of solvent mixtures, it was discovered that ACN:HFIP (1:1) afforded a 1:1.4 ratio of diastereomers (undesired favored, 26% total NMR yield). At this point, nearly 100 additional conditions were explored including waveform, temperature, electrolytes, solvents, electrodes, current density, and additives (see SI for details). These studies revealed that the desired product yield was diminished at higher conversions due to overoxidation. Therefore, all further efforts were focused on the suppression of overoxidation, reasoning that a solvent with a suitable oxidation window 13 might prevent undesired over-reactivity. This hypothesis proved fruitful, with substantial suppression of the overoxidized byproducts when enlisting an HFIP:DMSO mixture. Careful titration of the DMSO quantity proved essential to maintain oxidative efficiency whilst suppressing the formation of undesired products. More facile over-oxidation of the desired diastereomer was observed as evidenced by an apparent drop in dr at higher conversions, so reactions were run to partial conversion (ca. 50%) followed by recycling. Finally, the reaction was further enhanced using an uncommon ammonium fluorosulfate electrolyte.