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

2 Citations (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
Pages (from-to)2013-2017
Number of pages5
JournalSynlett
Volume31
Issue number20
DOIs
Publication statusPublished - Dec 17 2020

Keywords

  • Danishefsky's diene
  • Diels-Alder reaction
  • amino alcohols
  • asymmetric catalysis
  • nitrocoumarins
  • organocatalysis

ASJC Scopus subject areas

  • Organic Chemistry

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