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Iridium-catalyzed asymmetric double allylic alkylation of azlactone: efficient access to chiral α-amino acid derivatives.

Xiang ChengChong ShenXiu-Qin DongChun-Jiang Wang
Published in: Chemical communications (Cambridge, England) (2022)
An unprecedented Ir-catalyzed enantioselective double allylic alkylation of less bulky cyclic imine glycinate (azlactone) was rationally designed and developed, providing various bisallylated chiral amino acid derivatives. Control experiments revealed that this transformation proceeds in a sequential manner featuring quasi -dynamic kinetic resolution of the initially-formed monoallylation intermediates.
Keyphrases
  • amino acid
  • room temperature
  • ionic liquid
  • capillary electrophoresis
  • structure activity relationship
  • solid state
  • single cell
  • mass spectrometry