Iridium-Catalyzed Amidation of In SituPrepared Silyl Ketene Acetals to Access α-Amino Esters

Autor: Gwon, Yunyeong, Lee, Minhan, Kim, Dongwook, Chang, Sukbok
Zdroj: Organic Letters; February 2022, Vol. 24 Issue: 4 p1088-1093, 6p
Abstrakt: 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.
Databáze: Supplemental Index