Enantioselective diels-alder reaction of 3-nitrocoumarins promoted by chiral organoammonium salt catalysts

Yudai Fujii, Ryota Nakao, Saki Sugihara, Keita Fujita, Yuya Araki, Takayuki Kudoh, Ichiro Hayakawa, Haruki Mizoguchi, Akira Sakakura

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

An enantioselective Diels-Alder reaction of 3-nitrocoumarins has been developed. A tryptophan-derived C 1 -symmetric organoammonium thiourea catalyst promoted the reaction of 3-nitrocoumarins with Danishefsky's diene to give the corresponding adducts with good enantioselectivity (up to 94% ee). One of the resulting adducts was converted into a chiral carbocyclic quaternary β-amino alcohol.

Original languageEnglish
Article numberst-2020-u0431-l
JournalSynlett
DOIs
Publication statusAccepted/In press - 2020

Keywords

  • Amino alcohols
  • Asymmetric catalysis
  • Danishefsky's diene
  • Diels-Alder reaction
  • Nitrocoumarins
  • Organocatalysis

ASJC Scopus subject areas

  • Organic Chemistry

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