Iridium-Catalyzed Amidation of <i>In Situ</i> Prepared Silyl Ketene Acetals to Access α-Amino Esters
Yunyeong Gwon, Minhan Lee, Dongwook Kim, Sukbok Chang
Abstract
Disclosed herein is a convenient Ir-catalyzed amidation of esters to access α-amido esters. Initially prepared silyl ketene acetals are directly employed, without separate purification, for subsequent amidation with an oxycarbonylnitrenoid precursor using the Cp*(LX)Ir(III) catalyst. The α-amidation was facile for both α-aryl and α-alkyl esters. Density functional theory studies revealed that the generation of a putative Ir-nitrenoid is facilitated by the chelation of the countercation additive during the N-O bond cleavage of the nitrene precursor.
Topics & Concepts
KeteneChemistrySilylationIridiumCatalysisAlkylArylBond cleavageNitreneIn situCleavage (geology)Functional groupMedicinal chemistryCombinatorial chemistryOrganic chemistryPolymerGeotechnical engineeringFracture (geology)EngineeringSynthetic Organic Chemistry MethodsSynthesis and Catalytic ReactionsChemical Synthesis and Analysis