Enantioselective synthesis of N-C axially chiral indoles through chiral palladium-catalyzed 5-endo-hydroaminocyclization

Yudai Morimoto, Satoshi Shimizu, Ayano Mokuya, Nobutaka Ototake, Akio Saito, Osamu Kitagawa

Research output: Contribution to journalArticle

11 Citations (Scopus)


In the presence of (R)-SEGPHOS-PdCl<inf>2</inf> catalyst, 5-endo-hydroaminocyclization of various 2-(tert-butyl)-N-(2-ethynylphenyl)anilines proceeds enantioselectively to afford optically active N-C axially chiral N-(2-tert-butylphenyl)indole derivatives in good yields. The enantioselectivity depends strongly on the bulkiness of ortho-substituents and the electron density on the arylethynyl group, and it is explained by the dynamic axial chirality generated by the twisting of the aryl substituent.

Original languageEnglish
Publication statusAccepted/In press - 2015 Feb 20



  • Axial chirarity
  • Chiral phosphines
  • Hydroaminocyclization
  • Indoles
  • Palladium

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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