Enantioselective 1,3-Dipolar Cycloaddition Reaction of Nitrones with α-(Acyloxy)acroleins Catalyzed by Dipeptide-Derived Chiral Tri- or Diammonium Salts

Chihiro Kidou, Haruki Mizoguchi, Tatsuo Nehira, Akira Sakakura

Research output: Contribution to journalArticlepeer-review

Abstract

Organoammonium salts of dipeptide-derived chiral triamines or diamines with TfOH catalyzed the enantioselective 1,3-dipolar cycloaddition reactions of α-acyloxyacroleins with nitrones to give the corresponding adducts in good yields (up to 96%) and with high diastereo- and enantioselectivities (up to 89% ee). Although α-(p -methoxybenzoyloxy)acrolein is rather unstable under the reaction conditions, α-(3-pyrroline-1-carbonyloxy)acrolein is stable enough to be smoothly converted into the corresponding adducts with the aid of the chiral organoammonium salt catalysts.

Original languageEnglish
Pages (from-to)1835-1839
Number of pages5
JournalSynlett
Volume30
Issue number15
DOIs
Publication statusPublished - 2019

Keywords

  • 1,3-dipolar cycloaddition
  • acyloxyacroleins
  • asymmetric catalysis
  • isoxazolidines
  • nitrones
  • organocatalysis

ASJC Scopus subject areas

  • Organic Chemistry

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