Thieme Chemistry Journals Awardees - Where Are They Now? Bis(2-pyridyl)amides as Readily Cleavable Amides under Catalytic, Neutral, and Room-Temperature Conditions

Shinya Adachi, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

Mild solvolytic cleavage of bis(2-pyridyl)amide under neutral and room-temperature conditions is described. The inherently stable amide was readily activated by catalytic amounts of metal cations to react with alcohols. Based on X-ray crystallographic analysis, the primary driving force was considered to be amide distortion induced by the metal coordination of two pyridyl groups in a bidentate fashion without affecting the amide functionality. The compatibility of the acid/base-sensitive functionalities and the absence of racemization during solvolysis highlight the mildness of the present protocol.

Original languageEnglish
Pages (from-to)301-305
Number of pages5
JournalSynlett
Volume29
Issue number3
DOIs
Publication statusPublished - 2018 Feb 13
Externally publishedYes

Keywords

  • amide
  • amide distortion
  • amide twisting
  • deconjugation
  • metal coordination
  • mild conditions
  • solvolysis

ASJC Scopus subject areas

  • Organic Chemistry

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