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

10 Citations (Scopus)

Abstract

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
JournalTetrahedron
DOIs
Publication statusAccepted/In press - 2015 Feb 20

Fingerprint

Aniline Compounds
Indoles
Chirality
Enantioselectivity
Palladium
Carrier concentration
Derivatives
Catalysts
palladium chloride
indole

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Enantioselective synthesis of N-C axially chiral indoles through chiral palladium-catalyzed 5-endo-hydroaminocyclization. / Morimoto, Yudai; Shimizu, Satoshi; Mokuya, Ayano; Ototake, Nobutaka; Saito, Akio; Kitagawa, Osamu.

In: Tetrahedron, 20.02.2015.

Research output: Contribution to journalArticle

Morimoto, Yudai ; Shimizu, Satoshi ; Mokuya, Ayano ; Ototake, Nobutaka ; Saito, Akio ; Kitagawa, Osamu. / Enantioselective synthesis of N-C axially chiral indoles through chiral palladium-catalyzed 5-endo-hydroaminocyclization. In: Tetrahedron. 2015.
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AU - Ototake, Nobutaka

AU - Saito, Akio

AU - Kitagawa, Osamu

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