Practical Electrochemical Anodic Oxidation of Polycyclic Lactams for Late Stage Functionalization

摘要

Electrochemistry provides a powerful tool for the late-stage functionalization of complex lactams. A two-stage protocol for converting lactams, many of which are preparable through the intramolecular Schmidt reaction of keto azides, is presented. In the first step, anodic oxidation in MeOH using a repurposed power source provides a convenient route to lactams bearing a methoxy group adjacent to nitrogen. Treatment of these intermediates with a Lewis acid in DCM permits the regeneration of a reactive acyliminium ion that is then reacted with a range of nucleophilic species.