Enantioselective Aza-Friedel-Crafts Reaction of Heteroarenes with in situ Generated Isoxazolium Ions via Chiral Phosphoric Acid Catalysis

You Song Cheng, Shih Hsien Chan, Gunda Ananda Rao, Ramani Gurubrahamam, Kwunmin Chen*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

An asymmetric organocatalytic aza-Friedel-Crafts reaction was developed to give the enantioenriched Δ4-isoxazoline scaffold bearing a quaternary-substituted stereogenic centre in good-to-excellent yields and enantioselectivity (50–99%, 55–>99% ee). This protocol involves the in situ generated isoxazolium ions in the presence of a chiral phosphoric acid followed by the heteroarene addition through asymmetric counteranion-directed catalysis. (Figure presented.).

Original languageEnglish
Pages (from-to)3502-3506
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume363
Issue number14
DOIs
Publication statusPublished - 2021 Jul 20

Keywords

  • 2,3-dihydroisoxazole
  • aza-Friedel-Crafts reaction
  • chiral phosphoric acid
  • ion-pair catalysis
  • organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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