Practical Electrochemical Anodic Oxidation of Polycyclic Lactams for Late Stage Functionalization.

Angewandte Chemie (International ed. in English)

PubMedID: 26371961

Frankowski KJ, Liu R, Milligan GL, Moeller KD, Aubé J. Practical Electrochemical Anodic Oxidation of Polycyclic Lactams for Late Stage Functionalization. Angew Chem Int Ed Engl. 2015;54(36):10555-8.
Electrochemistry provides a powerful tool for the late-stage functionalization of complex lactams. A two-stage protocol for converting lactams, many of which can be prepared 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 dichloromethane permits the regeneration of a reactive acyliminium ion that is then reacted with a range of nucleophilic species.