To evaluate the regioselectivity of the reaction, we continued our investigation with protected ornithine and lysine derivatives bearing two carbamate groups (Scheme 3). Direct anodic oxidation of Boc-Lys(Boc)-OMe (1l) without NaCl as mediator gave -methoxylated lysine 3l selectively. Methoxylation of the -position was not observed. The faradaic efficiency and yield of this process were low. Application of our optimized conditions resulted in low faradaic efficiency and limited regioselectivity leading to an inseparable mixture of -, -, and dimethoxylated products. Fortunately, running the reaction without LiClO4 as additional conducting salt showed high selectivity for the -position. As previously discussed, the conversion stalled after 10 F/mol, probably due to passivation of the anode surface. Scheme 3. Regioselectivity of the anodic oxidation of lysine and ornithine derivatives.