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

doi:10.1016/j.tet.2015.05.001

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 journal › Article › peer-review

33 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 language	English
Pages (from-to)	5221-5229
Number of pages	9
Journal	Tetrahedron
Volume	72
Issue number	34
DOIs	https://doi.org/10.1016/j.tet.2015.05.001
Publication status	Published - 2016

Keywords

Axial chirarity
Chiral phosphines
Hydroaminocyclization
Indoles
Palladium

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2015.05.001

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title = "Enantioselective synthesis of N–C axially chiral indoles through chiral palladium-catalyzed 5-endo-hydroaminocyclization",

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.",

keywords = "Axial chirarity, Chiral phosphines, Hydroaminocyclization, Indoles, Palladium",

author = "Yudai Morimoto and Satoshi Shimizu and Ayano Mokuya and Nobutaka Ototake and Akio Saito and Osamu Kitagawa",

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pages = "5221--5229",

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T1 - Enantioselective synthesis of N–C axially chiral indoles through chiral palladium-catalyzed 5-endo-hydroaminocyclization

AU - Morimoto, Yudai

AU - Shimizu, Satoshi

AU - Mokuya, Ayano

AU - Ototake, Nobutaka

AU - Saito, Akio

AU - Kitagawa, Osamu

PY - 2016

Y1 - 2016

N2 - 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.

AB - 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.

KW - Axial chirarity

KW - Chiral phosphines

KW - Hydroaminocyclization

KW - Indoles

KW - Palladium

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U2 - 10.1016/j.tet.2015.05.001

DO - 10.1016/j.tet.2015.05.001

M3 - Article

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VL - 72

SP - 5221

EP - 5229

JO - Tetrahedron

JF - Tetrahedron

IS - 34

ER -

Enantioselective synthesis of N–C axially chiral indoles through chiral palladium-catalyzed 5-endo-hydroaminocyclization

Abstract

Keywords

ASJC Scopus subject areas

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