Conquering amide planarity: Structural distortion and its hidden reactivity

Shinya Adachi, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalReview articlepeer-review

48 Citations (Scopus)


Amides are generally considered as a low-reactive chemical entity among the carbonyl group, and therefore fewer opportunities to be involved in catalytic transformations as substrates. The origin of the stable nature of amides is resonance stabilization in the planar structure, which has drawn considerable attention from organic and physical chemists, leading to the discovery of distorted amides that exhibit a substantially reactive nature. Recent focus in this field is on the catalytic transformation of designed amides with moderate distortion or reduced resonance stabilization. This digest reviews the brief history of the quest for highly distorted amides and introduces a collection of recent studies on catalytic transformations of designed amides.

Original languageEnglish
Pages (from-to)1147-1158
Number of pages12
JournalTetrahedron Letters
Issue number13
Publication statusPublished - 2018 Mar 28
Externally publishedYes


  • Amide
  • Amide planarity
  • Amide pyramidalization
  • Catalysis
  • Twisted amide

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


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