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 journalArticlepeer-review

17 Citations (Scopus)

Abstract

In the presence of (R)-SEGPHOS-PdCl2catalyst, 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
Pages (from-to)5221-5229
Number of pages9
JournalTetrahedron
Volume72
Issue number34
DOIs
Publication statusPublished - 2016

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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