Acceleration of a dipolar cycloaddition by a simple bisamide receptor

Heidi L. Rowe, Neil Spencer, Douglas Philp

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

A bisamide receptor has been synthesized which is capable of binding and, hence, polarizing maleimide. The hydrogen bonds formed between the receptor and maleimide alter its inherent reactivity. Full kinetic investigations, performed using 1H NMR spectroscopy and computer-based simulation, reveal that the formation of the 1:1 complex increases the rate of the cycloaddition between maleimide and diphenylnitrone fivefold. (C) 2000 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)4475-4479
Number of pages5
JournalTetrahedron Letters
Volume41
Issue number22
DOIs
StatePublished - Jun 8 2000

Keywords

  • Catalysis
  • Cycloadditions
  • Hydrogen bonding
  • Isoxazolidines

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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