Recognition-mediated facilitation of a disfavored Diels - Alder reaction

Raphaël Bennes, Douglas Philp*, Neil Spencer, Benson M. Kariuki, Kenneth D.M. Harris

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

Abstract

(matrix presented) The rational design of a system which is capable of accelerating and facilitating a thermodynamically disfavored Diels-Alder cycloaddition between a furan and a maleimide is presented. The origins of the acceleration and facilitation of the cycloaddition reaction are traced by kinetic studies-allied to results from 1H NMR spectroscopy and X-ray crystallography-to the formation of strong intramolecular hydrogen bonds in the cycloadduct.

Original languageEnglish (US)
Pages (from-to)1087-1090
Number of pages4
JournalOrganic Letters
Volume1
Issue number7
DOIs
StatePublished - Oct 7 1999

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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