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査読

20 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)5221-5229
ページ数9
ジャーナルTetrahedron
72
34
DOI
出版ステータスPublished - 2016

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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