Catalytic enantioselective synthesis of atropisomeric indoles with an N-C chiral axis

Nobutaka Ototake; Yudai Morimoto; Ayano Mokuya; Haruhiko Fukaya; Yasuo Shida; Osamu Kitagawa

doi:10.1002/chem.201000243

Catalytic enantioselective synthesis of atropisomeric indoles with an N-C chiral axis

Nobutaka Ototake, Yudai Morimoto, Ayano Mokuya, Haruhiko Fukaya, Yasuo Shida, Osamu Kitagawa

Research output: Contribution to journal › Article › peer-review

99 Citations (Scopus)

Abstract

(Chemical Equation Presented) A pivotal role: In the presence of (R)-(-)-5,5′-bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4, 4′-bi-1,3-benzodioxole-PdCl₂ [(R)-SEGPHOS-PdCl₂], 5-endo-hydroaminocyclization of achiral ortho-alkynylanilines proceeds in an enantioselective manner to give optically active, axially chiral indoles (see scheme).

Original language	English
Pages (from-to)	6752-6755
Number of pages	4
Journal	Chemistry - A European Journal
Volume	16
Issue number	23
DOIs	https://doi.org/10.1002/chem.201000243
Publication status	Published - 2010 Jun 18

Keywords

Atropisomerism
Enantioselectivity
Indoles
Palladium
Phosphane ligands

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201000243

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title = "Catalytic enantioselective synthesis of atropisomeric indoles with an N-C chiral axis",

abstract = "(Chemical Equation Presented) A pivotal role: In the presence of (R)-(-)-5,5′-bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4, 4′-bi-1,3-benzodioxole-PdCl2 [(R)-SEGPHOS-PdCl2], 5-endo-hydroaminocyclization of achiral ortho-alkynylanilines proceeds in an enantioselective manner to give optically active, axially chiral indoles (see scheme).",

keywords = "Atropisomerism, Enantioselectivity, Indoles, Palladium, Phosphane ligands",

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T1 - Catalytic enantioselective synthesis of atropisomeric indoles with an N-C chiral axis

AU - Ototake, Nobutaka

AU - Morimoto, Yudai

AU - Mokuya, Ayano

AU - Fukaya, Haruhiko

AU - Shida, Yasuo

AU - Kitagawa, Osamu

PY - 2010/6/18

Y1 - 2010/6/18

N2 - (Chemical Equation Presented) A pivotal role: In the presence of (R)-(-)-5,5′-bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4, 4′-bi-1,3-benzodioxole-PdCl2 [(R)-SEGPHOS-PdCl2], 5-endo-hydroaminocyclization of achiral ortho-alkynylanilines proceeds in an enantioselective manner to give optically active, axially chiral indoles (see scheme).

AB - (Chemical Equation Presented) A pivotal role: In the presence of (R)-(-)-5,5′-bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4, 4′-bi-1,3-benzodioxole-PdCl2 [(R)-SEGPHOS-PdCl2], 5-endo-hydroaminocyclization of achiral ortho-alkynylanilines proceeds in an enantioselective manner to give optically active, axially chiral indoles (see scheme).

KW - Atropisomerism

KW - Enantioselectivity

KW - Indoles

KW - Palladium

KW - Phosphane ligands

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JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

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Catalytic enantioselective synthesis of atropisomeric indoles with an N-C chiral axis

Abstract

Keywords

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