Synthesis of a C1-symmetric box macrocycle and studies toward active template synthesis of mechanically planar chiral rotaxanes

Pauline Elizabeth Glen, James Alan Thomas O'Neill, Ai-Lan Lee

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

A C-1-symmetric Box macrocycle has been synthesized for the first time. The Box macrocycle along with other C-1 and C-2-symmetric Box ligands were evaluated and compared as ligands in the Cadiot-Chodkiewicz, oxidative Heck and CuAAC 'click' reactions as part of our studies towards achieving active-metal template synthesis of mechanically planar chiral rotaxanes. This study constitutes the first report of Cadiot-Chodkiewicz and CuAAC 'click' reactions using Box ligands, as well as the first dedicated study of oxidative Heck reactions using Box ligands. (C) 2012 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)57-68
Number of pages12
JournalTetrahedron
Volume69
Issue number1
DOIs
Publication statusPublished - 7 Jan 2013

Keywords

  • Macrocycles
  • Bis-oxazolines
  • Oxidative Heck
  • CuAAC click
  • Cadiot-Chodkiewicz
  • Rotaxane
  • HECK-TYPE REACTION
  • CLICK CHEMISTRY
  • CYCLOPROPANATION REACTIONS
  • BIS(OXAZOLINE) LIGANDS
  • ASYMMETRIC CATALYSIS
  • MOLECULAR SHUTTLES
  • C-2-SYMMETRIC LIGANDS
  • COMPLEXES
  • CATENANES
  • RESOLUTION

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