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Issue 3, 2014
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An efficient Cu(ii)-bis(oxazoline)-based polymer immobilised ionic liquid phase catalyst for asymmetric carbon–carbon bond formation

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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.

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

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Supplementary files

Article information


Submitted
11 Jul 2013
Accepted
09 Dec 2013
First published
09 Dec 2013

This article is Open Access

Green Chem., 2014,16, 1470-1479
Article type
Paper

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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