Synthesis and NMR binding studies towards rational design of a series of electron-withdrawing diamide receptors/organocatalysts

Michael Kinsella, Patrick Duggan, Jimmy Muldoon, Kevin S. Eccles, Simon E. Lawrence, Claire Lennon

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

A related series of bisamides have been evaluated for rational correlation between anion complexation and organocatalysis: remarkable enhancement of hydrogen bonding to anions was observed along with significant increases in catalytic activity in the Baylis-Hillman reaction. In addition, X-ray crystallography showed a large degree of pre-organisation was observed in one receptor by incorporation of bis(trifluoromethyl)aniline groups along with a thioamide functionality. A novel bifunctional amide/N-acylsulfonamide within the series gave the best catalytic profile.

Original languageEnglish
Pages (from-to)1125-1132
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number6
DOIs
Publication statusPublished - Feb 2011

Keywords

  • Amides
  • Anion binding
  • Anions
  • H-bonding
  • Organocatalysis

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