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

研究成果: Article

11 引用 (Scopus)

抄録

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.

元の言語English
ジャーナルTetrahedron
DOI
出版物ステータスAccepted/In press - 2015 2 20

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

これを引用

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.

:: Tetrahedron, 20.02.2015.

研究成果: Article

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. :: Tetrahedron. 2015.
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AU - Morimoto, Yudai

AU - Shimizu, Satoshi

AU - Mokuya, Ayano

AU - Ototake, Nobutaka

AU - Saito, Akio

AU - Kitagawa, Osamu

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AB - In the presence of (R)-SEGPHOS-PdCl2 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.

KW - Axial chirarity

KW - Chiral phosphines

KW - Hydroaminocyclization

KW - Indoles

KW - Palladium

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