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

Lookup NU author(s): Dr Simon DohertyORCiD, Dr Julian Knight, Jack Ellison

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This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).

Abstract

The asymmetric carbon-carbon bond forming reactions such as the 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 branched ionic polymers. In both reactions selectivity and ee were strongly influenced by the choice of polymer. A comparison of the performance of Cu(II)-bis(oxazoline)-PIILP catalyst against analogous supported ionic liquid phase (SILP) heterogeneous catalysts as well as their homogeneous counterparts has been undertaken and their relative merits evaluated.

Publication metadata

Author(s): Doherty S, Knight JG, Ellison JR, Goodrich P, Hall L, Hardacre C, Muldoon M, Ribeiro A, Afonso C, Park S, Lourençoc MJ, Davey P

Publication type: Article

Publication status: Published

Journal: Green Chemistry

Year: 2014

Volume: 16

Issue: 3

Pages: 1470-1479

Print publication date: 01/03/2014

Online publication date: 09/12/2013

Acceptance date: 09/12/2013

Date deposited: 16/12/2014

ISSN (print): 1463-9262

ISSN (electronic): 1463-9270

Publisher: RSC Publications

URL: http://dx.doi.org/10.1039/c3gc41378k

DOI: 10.1039/c3gc41378k

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