Recognition-induced Acceleration and Regiocontrol of a [3+2] Dipolar CycloadditionReaction

SJ Howell, Douglas Philp, N Spencer

Research output: Contribution to journalArticlepeer-review

59 Citations (Scopus)

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. (C) 2001 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)4945-4954
Number of pages10
JournalTetrahedron
Volume57
Publication statusPublished - 4 Jun 2001

Keywords

  • azides
  • cycloaddition
  • kinetics
  • molecular recognition
  • DIELS-ALDER REACTION
  • INTRAMOLECULAR REACTIONS
  • CATALYSIS
  • ACCELERATION
  • ENERGETICS
  • MIMICS
  • MODELS

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