Enantioselective Formal C−H Conjugate Addition of Acetanilides to β-Substituted Acrylates by Chiral Iridium Catalysts

Takanori Shibata, Masamichi Michino, Hisaki Kurita, Yu Ki Tahara, Stephen Kyalo Kanyiva

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The Ir-catalyzed enantioselective reaction of substituted acetanilides with β-substituted α,β-unsaturated esters provided chiral 3,3-disubstituted propanoates in high yield with good-to-excellent enantiomeric excess (up to 99 % ee). This transformation, initiated by sp2 C−H bond activation, is the first example of enantioselective formal C−H conjugate addition to β-substituted α,β-unsaturated carbonyl compounds. The starting materials are commercially available and/or readily accessible.

Original languageEnglish
Pages (from-to)88-91
Number of pages4
JournalChemistry - A European Journal
Volume23
Issue number1
DOIs
Publication statusPublished - 2017 Jan 1

Keywords

  • acetanilides
  • conjugate addition
  • C−H alkylation
  • enantioselective
  • iridium

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'Enantioselective Formal C−H Conjugate Addition of Acetanilides to β-Substituted Acrylates by Chiral Iridium Catalysts'. Together they form a unique fingerprint.

  • Cite this