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

13 引用 (Scopus)

抜粋

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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