Recognition-mediated regiocontrol of a dipolar cycloaddition reaction

Sarah J. Howell, Neil Spencer, Douglas Philp*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

59 Scopus citations

Abstract

The rational design of a recognition-based system that is capable of accelerating and controlling the regiochemical outcome of a dipolar cycloaddition reaction between an azide and an alkyne is presented. The origins of the acceleration and control of the cycloaddition reactions are rationalized - using molecular mechanics calculations - in terms of the formation of a complex between the reagents which organizes and orients them prior to reaction.

Original languageEnglish (US)
Pages (from-to)4945-4954
Number of pages10
JournalTetrahedron
Volume57
Issue number23
DOIs
StatePublished - Jun 4 2001

Keywords

  • Azides
  • Cycloaddition
  • Kinetics
  • Molecular recognition

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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