Issue 3, 2014

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
11 Jul 2013
Accepted
09 Dec 2013
First published
09 Dec 2013
This article is Open Access
Creative Commons BY license

Green Chem., 2014,16, 1470-1479

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

S. Doherty, J. G. Knight, J. R. Ellison, P. Goodrich, L. Hall, C. Hardacre, M. J. Muldoon, S. Park, A. Ribeiro, C. A. N. de Castro, M. J. Lourenço and P. Davey, Green Chem., 2014, 16, 1470 DOI: 10.1039/C3GC41378K

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