Ir-Catalyzed Enantioselective Intra- and Intermolecular Formal C−H Conjugate Addition to β-Substituted α,β-Unsaturated Esters

Takanori Shibata, Hisaki Kurita, Sahoko Onoda, Stephen Kyalo Kanyiva

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

An enantioselective intramolecular formal C−H conjugate addition of 4-methyl 1-aryl 2-methylfumarates proceeded using a chiral iridium catalyst. A benzoylamide group served as a directing group, and chiral γ-lactones with a quaternary all-carbon stereogenic center were obtained with up to excellent ee. In the intermolecular reaction of N-arylbenzamides with β-substituted acrylates, C−H bond activation selectively occurred at the ortho-position of carbonyl groups, and highly enantioselective formal C−H conjugate addition proceeded.

Original languageEnglish
Pages (from-to)1411-1418
Number of pages8
JournalAsian Journal of Organic Chemistry
Volume7
Issue number7
DOIs
Publication statusPublished - 2018 Jul 1

Keywords

  • acrylates
  • conjugate addition
  • C−H alkylation
  • enantioselectivity
  • iridium

ASJC Scopus subject areas

  • Organic Chemistry

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