Nucleophilic and Electrophilic Activation of Non-Heteroaromatic Amides in Atom-Economical Asymmetric Catalysis

Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalReview articlepeer-review

24 Citations (Scopus)

Abstract

Recent advances in catalytic asymmetric carbon–carbon bond-forming reactions of non-heteroaromatic amide substrates are highlighted. Among carbonyl compounds, amides have received limited attention in catalytic asymmetric transformations mainly owing to their lower reactivity. Amides are reluctant to form enolates for nucleophilic addition, and α,β-unsaturated amides exhibit diminished electrophilicity at the β-carbon. Recent advances in asymmetric catalysis rendered these amides amenable to enantioselective reactions with perfect atom economy, producing synthetically useful chiral building blocks. This Minireview summarizes recent developments in the field.

Original languageEnglish
Pages (from-to)15192-15200
Number of pages9
JournalChemistry - A European Journal
Volume22
Issue number43
DOIs
Publication statusPublished - 2016 Oct 17
Externally publishedYes

Keywords

  • C−C coupling
  • amides
  • asymmetric catalysis
  • atom economy
  • synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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