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Phenolic Dienes as Highly Selective Dienophiles in the Asymmetric Organocatalyzed Three-Component Vinylogous Povarov Reaction.

Aurélien BrionVittoria MartiniMarine LombardPascal RetailleauNicola Della Ca'Luc NeuvilleGeraldine Masson
Published in: The Journal of organic chemistry (2024)
Our study presents a novel enantioselective route for the synthesis of 1,2,3,4-tetrahydroquinolines via a chiral phosphoric acid-catalyzed three-component Povarov reaction, employing phenolic dienes as dienophiles. This approach produces a diverse array of 2,3,4-trisubstituted tetrahydroquinolines, each featuring a styryl group at position 4, in high yields with excellent regio-, diastereo-, and enantioselectivities (>95:5 dr and up to >99% ee).
Keyphrases
  • high resolution
  • room temperature
  • electron transfer
  • high density