Login / Signup

Iridium-Catalyzed Amidation of In Situ Prepared Silyl Ketene Acetals to Access α-Amino Esters.

Yunyeong GwonMinhan LeeDongwook KimSukbok Chang
Published in: Organic letters (2022)
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.
Keyphrases
  • density functional theory
  • room temperature
  • ionic liquid
  • molecular dynamics
  • highly efficient
  • reduced graphene oxide
  • metal organic framework
  • case control