An efficient Cu(II)-bis(oxazoline)-based polymer immobilised ionic liquid phase catalyst for asymmetric carbon–carbon bond formation

Simon Doherty, Julian G. Knight, Jack R. Ellison, Peter Goodrich, Leanne Hall, Christopher Hardacre, Mark J. Muldoon, Soomin Park, Ana Ribeiro, Carlos Alberto Nieto de Castro, Maria José Lourenço, Paul Davey

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Abstract

The asymmetric Diels-Alder reaction between N-acryloyloxazolidinone and cyclopentadiene and the Mukaiyama-aldol reaction between methylpyruvate and 1-phenyl-1-trimethylsilyloxyethene have been catalysed by heterogeneous copper(II)-bis(oxazoline)-based polymer immobilised ionic liquid phase (PIILP) systems generated from a range of linear and cross linked ionic polymers. In both reactions selectivity and ee were strongly influenced by the choice of polymer. A comparison of the performance of a range of Cu(II)-bis(oxazoline)-PIILP catalyst systems against analogous supported ionic liquid phase (SILP) heterogeneous catalysts as well as their homogeneous counterparts has been undertaken and their relative merits evaluated.

Original languageEnglish
Pages (from-to)1470-1479
Number of pages10
JournalGreen Chemistry
Volume16
Issue number3
Early online date09 Dec 2013
DOIs
Publication statusPublished - 01 Mar 2014

Keywords

  • DIELS-ALDER REACTION
  • MUKAIYAMA ALDOL REACTION
  • ENANTIOSELECTIVE CYCLOPROPANATION REACTIONS
  • CHIRAL CATALYSTS
  • BIS(OXAZOLINE)-COPPER COMPLEXES
  • HETEROGENEOUS CATALYST
  • METAL-COMPLEXES
  • CYCLOPENTADIENE
  • SUPPORT

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