Piperidine-derived substrates decorated with a cyano group, a spiro center, or a fluorinated benzisoxazole all proved compatible, giving the corresponding products 5f-5h in good yields (60-75%). Lactam 4i housing two potential sites for C-H bond functionalization displayed a preference to undergo site-selective functionalization at the methyl position, resulting in exclusive formation of one regioisomer in 72% yield. Next, various nitrogenbased protecting groups were evaluated. We observed a significant increase in yield up to 79% when the nitrogen center was protected with a pyrimidine moiety as in product 5j. The benzyloxycarbonyl (Cbz) and benzoyl (Bz) protecting groups afforded the corresponding αamino acid derivatives 5k and 5l in 59% and 43% yield, respectively. However, the benzyl (Bn) protecting group yielded only 19% of the desired product 5m.