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Modular Tuning of Electrophilic Reactivity of Iridium Nitrenoids for the Intermolecular Selective α‑Amidation of β‑Keto Esters

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posted on 03.07.2020 by Minhan Lee, Hoimin Jung, Dongwook Kim, Jung-Woo Park, Sukbok Chang
We report herein an Ir-catalyzed intermolecular amino group transfer to β-keto esters (amides) to access α-aminocarbonyl products with excellent chemoselectivity. The key strategy was to engineer electrophilicity of the putative Ir-nitrenoids by tuning electronic property of the κ2-N,O chelating ligands, thus facilitating nucleophilic addition of enol π-bonds of 1,3-dicarbonyl substrates.