Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 36, Pages 10555-10558Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201504775
Keywords
anodic oxidation; diversity-oriented synthesis; heterocycles; lactams; N-acyliminium ions
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Funding
- National Institute of General Medical Sciences [PO50-GM069663]
- NSF-MRI grant [CHE-0923449]
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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.
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