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

Research output: Contribution to journalArticle

14 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)14272-14276
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number45
DOIs
Publication statusPublished - Nov 6 2017
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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