Recognition-induced control of a Diels-Alder cycloaddition

Andrew Robertson, Douglas Philp, Neil Spencer

Research output: Contribution to journalArticlepeer-review

36 Citations (Scopus)

Abstract

The rational design of systems which are capable of accelerating and/or controlling the stereochemical outcome of the Diels-Alder cycloaddition reaction between a furan and a maleimide is presented. The origins of the acceleration and control of the cycloaddition reactions are traced by kinetic studies - allied to molecular mechanics calculations - to the formation of complexes in which the dienes and the dieneophiles are placed in the appropriate arrangements for reaction, and, more importantly, to the formation of intramolecular hydrogen bonds in the cycloadducts.

Original languageEnglish
Pages (from-to)11365-11384
Number of pages20
JournalTetrahedron
Volume55
Issue number37
DOIs
Publication statusPublished - Sep 10 1999
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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