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Chiral Aldehyde-Palladium Catalysis Enables Asymmetric Synthesis of α-Alkyl Tryptophans via Cascade Heck-Alkylation Reaction.

Qi-Wen ShenWei WenQi-Xiang Guo
Published in: Organic letters (2023)
The first catalytic asymmetric cascade Heck-alkylation reaction of NH 2 -unprotected amino acid esters with N -(2-iodophenyl)allenamides is reported in this work. Under the promotion of a combining catalytic system comprising a chiral aldehyde, a chiral palladium complex, and the Lewis acid ZnCl 2 , the title reaction takes place smoothly, giving optically active α-alkyl tryptophan derivatives in moderate to good yields and excellent enantioselectivities. The target products can be converted into other structurally complex chiral indoles without the loss of enantioselectivities.
Keyphrases
  • ionic liquid
  • capillary electrophoresis
  • amino acid
  • room temperature
  • mass spectrometry
  • reduced graphene oxide
  • high intensity
  • visible light