Asymmetric Cycloisomerization of o-Alkenyl-N-Methylanilines to Indolines by Iridium-Catalyzed C(sp3)−H Addition to Carbon–Carbon Double Bonds

Takeru Torigoe, Toshimichi Ohmura, Michinori Suginome

研究成果: ジャーナルへの寄稿記事

8 引用 (Scopus)

抄録

Highly enantioselective cycloisomerization of N-methylanilines, bearing o-alkenyl groups, into indolines is established. An iridium catalyst bearing a bidentate chiral diphosphine effectively promotes the intramolecular addition of the C(sp3)−H bond across a carbon–carbon double bond in a highly enantioselective fashion. The reaction gives indolines bearing a quaternary stereogenic carbon center at the 3-position. The reaction mechanism involves rate-determining oxidative addition of the N-methyl C−H bond, followed by intramolecular carboiridation and subsequent reductive elimination.

元の言語英語
ページ(範囲)14272-14276
ページ数5
ジャーナルAngewandte Chemie - International Edition
56
発行部数45
DOI
出版物ステータス出版済み - 11 6 2017

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Bearings (structural)
Iridium
Carbon
Catalysts
indoline
methylaniline

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

これを引用

Asymmetric Cycloisomerization of o-Alkenyl-N-Methylanilines to Indolines by Iridium-Catalyzed C(sp3)−H Addition to Carbon–Carbon Double Bonds. / Torigoe, Takeru; Ohmura, Toshimichi; Suginome, Michinori.

:: Angewandte Chemie - International Edition, 巻 56, 番号 45, 06.11.2017, p. 14272-14276.

研究成果: ジャーナルへの寄稿記事

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abstract = "Highly enantioselective cycloisomerization of N-methylanilines, bearing o-alkenyl groups, into indolines is established. An iridium catalyst bearing a bidentate chiral diphosphine effectively promotes the intramolecular addition of the C(sp3)−H bond across a carbon–carbon double bond in a highly enantioselective fashion. The reaction gives indolines bearing a quaternary stereogenic carbon center at the 3-position. The reaction mechanism involves rate-determining oxidative addition of the N-methyl C−H bond, followed by intramolecular carboiridation and subsequent reductive elimination.",
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