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Merging Visible-Light Photoredox and Chiral Phosphate Catalysis for Asymmetric Friedel-Crafts Reaction with in Situ Generation of N-Acyl Imines.

Meng-Lan ShenYang ShenPu-Sheng Wang
Published in: Organic letters (2019)
In the presence of visible-light photoredox and chiral phosphate catalysts, a novel asymmetric Friedel-Crafts reaction of indoles and readily accessible α-amino acid derived redox-active esters is established to afford enantioenriched 1-indolyl-1-alkylamine derivatives in moderate to high yields and with high levels of enantioselectivities. This method not only shows a mild and efficient alternative for the in situ generation of N-acyl imines but also indicates the feasibility of a multicatalyst system for asymmetric photoredox catalysis.
Keyphrases
  • visible light
  • amino acid
  • solid state
  • capillary electrophoresis
  • ionic liquid
  • fatty acid
  • electron transfer
  • high intensity
  • highly efficient
  • structure activity relationship