Synergistic Catalysis: Highly Enantioselective Cascade Reaction for the Synthesis of Dihydroacridines

Sara Meninno, Marta Meazza, Jung Woon Yang, Tomas Tejero, Pedro Merino-Gomez, Ramon Rios

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

The first stereoselective synthesis of dihydroacridines through synergistic catalysis, achieving the final target compounds with good to excellent yields and good to excellent enantioselectivities and diastereoselectivities, is reported. The synergistic approach consists in the activation of substituted quinolines with a Lewis acid catalyst that react in a cascade fashion with activated enals in the iminium form. Mechanistic calculations support a consecutive Michael–aldol reaction, followed by dehydration.

Original languageBritish English
Pages (from-to)7623-7627
Number of pages5
JournalChemistry - A European Journal
Volume25
Issue number32
DOIs
StatePublished - 7 Jun 2019

Keywords

  • acridine
  • diastereoselective
  • enantioselective
  • synergistic catalysis
  • ytterbium

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