Modular Tuning of Electrophilic Reactivity of Iridium Nitrenoids for the Intermolecular Selective α-Amidation of β-Keto Esters
Minhan Lee, Hoimin Jung, Dongwook Kim, Jung‐Woo Park, Sukbok Chang
Abstract
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.
Topics & Concepts
ChemistryIridiumElectrophileChemoselectivityNucleophileIntermolecular forceReactivity (psychology)UmpolungCombinatorial chemistryNucleophilic additionChelationMedicinal chemistryCatalysisOrganic chemistryMoleculeAlternative medicinePathologyMedicineSynthesis and Catalytic ReactionsChemical Synthesis and AnalysisAdvanced Synthetic Organic Chemistry