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Updated: Jan 10, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Oxidative α-Amination and Aziridination of Cyclic β-Ketoesters Using Aminobenziodoxolones
Kazuki Kawanaka1, Kotaro Muraoka1, Kensuke Kiyokawa1
1Department of Applied Chemistry, Graduate School of Engineering, The University of Osaka, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan.
Abstract:
The oxidative amination of β-ketoesters with hypervalent iodine reagents bearing transferable amino groups (aminobenziodoxolones) is described. NH2-substituted and alkylamine-derived aminobenziodoxolones enable electrophilic α-amination, whereas the use of arylamine-derived reagents promotes aziridination to afford fused aziridines. The developed methods expand the scope of accessible α-amino-β-ketoester scaffolds, which represent unique and valuable synthetic intermediates for the construction of nitrogen-containing compounds.
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