Electrophilic α‑Amination Reaction of β‑Ketoesters Using N‑Hydroxycarbamates: Merging Aerobic Oxidation and Lewis Acid Catalysis

The copper-catalyzed α-amination of carbonyl compounds using nitrosoformate intermediates as the electrophilic source of nitrogen is reported. The reaction merges aerobic oxidation and Lewis acid catalysis. The scope of the reaction is broad in terms of both the N-substituted hydroxylamines and the...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2012-11, Vol.134 (46), p.18948-18951
Main Authors: Sandoval, David, Frazier, Charles P, Bugarin, Alejandro, Read de Alaniz, Javier
Format: Article
Language:English
Subjects:
Aerobiosis
Amination
Carbamates - chemistry
Catalysis
Esters - chemistry
Lewis Acids - chemistry
Oxidation-Reduction
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Summary:The copper-catalyzed α-amination of carbonyl compounds using nitrosoformate intermediates as the electrophilic source of nitrogen is reported. The reaction merges aerobic oxidation and Lewis acid catalysis. The scope of the reaction is broad in terms of both the N-substituted hydroxylamines and the β-ketoesters. The new methodology harnesses the power of nitrosoformate intermediates and demonstrates their potential as a viable electrophilic source of nitrogen in α-functionalization reactions.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja310784f