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Practical Electrochemical Anodic Oxidation of Polycyclic Lactams for Late Stage Functionalization
Author(s) -
Frankowski Kevin J.,
Liu Ruzhang,
Milligan Gregory L.,
Moeller Kevin D.,
Aubé Jeffrey
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201504775
Subject(s) - surface modification , intramolecular force , dichloromethane , chemistry , electrochemistry , nucleophile , lewis acids and bases , combinatorial chemistry , anodic oxidation , anode , nucleophilic addition , organic chemistry , electrode , catalysis , solvent
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.