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

doi:10.1039/c3gc41378k

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

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article › peer-review

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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 language	English
Pages (from-to)	1470-1479
Number of pages	10
Journal	Green Chemistry
Volume	16
Issue number	3
Early online date	09 Dec 2013
DOIs	https://doi.org/10.1039/c3gc41378k
Publication status	Published - 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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10.1039/c3gc41378k

An efficient Cu(II)-bis(oxazoline)-based polymer immobilised ionic liquid phase catalyst for asymmetric carbon–carbon bond formation
© 2014 The Authors This is an open access article published under a Creative Commons Attribution License (https://creativecommons.org/licenses/by/3.0/), which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
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Doherty, S., Knight, J. G., Ellison, J. R., Goodrich, P., Hall, L., Hardacre, C., Muldoon, M. J., Park, S., Ribeiro, A., Nieto de Castro, C. A., Lourenço, M. J., & Davey, P. (2014). An efficient Cu(II)-bis(oxazoline)-based polymer immobilised ionic liquid phase catalyst for asymmetric carbon–carbon bond formation. Green Chemistry, 16(3), 1470-1479. https://doi.org/10.1039/c3gc41378k

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title = "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.",

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

author = "Simon Doherty and Knight, {Julian G.} and Ellison, {Jack R.} and Peter Goodrich and Leanne Hall and Christopher Hardacre and Muldoon, {Mark J.} and Soomin Park and Ana Ribeiro and {Nieto de Castro}, {Carlos Alberto} and Louren{\c c}o, {Maria Jos{\'e}} and Paul Davey",

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doi = "10.1039/c3gc41378k",

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publisher = "Royal Society of Chemistry",

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Doherty, S, Knight, JG, Ellison, JR, Goodrich, P, Hall, L, Hardacre, C, Muldoon, MJ, Park, S, Ribeiro, A, Nieto de Castro, CA, Lourenço, MJ & Davey, P 2014, 'An efficient Cu(II)-bis(oxazoline)-based polymer immobilised ionic liquid phase catalyst for asymmetric carbon–carbon bond formation', Green Chemistry, vol. 16, no. 3, pp. 1470-1479. https://doi.org/10.1039/c3gc41378k

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T1 - An efficient Cu(II)-bis(oxazoline)-based polymer immobilised ionic liquid phase catalyst for asymmetric carbon–carbon bond formation

AU - Doherty, Simon

AU - Knight, Julian G.

AU - Ellison, Jack R.

AU - Goodrich, Peter

AU - Hall, Leanne

AU - Hardacre, Christopher

AU - Muldoon, Mark J.

AU - Park, Soomin

AU - Ribeiro, Ana

AU - Nieto de Castro, Carlos Alberto

AU - Lourenço, Maria José

AU - Davey, Paul

PY - 2014/3/1

Y1 - 2014/3/1

N2 - 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.

AB - 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.

KW - DIELS-ALDER REACTION

KW - MUKAIYAMA ALDOL REACTION

KW - ENANTIOSELECTIVE CYCLOPROPANATION REACTIONS

KW - CHIRAL CATALYSTS

KW - BIS(OXAZOLINE)-COPPER COMPLEXES

KW - HETEROGENEOUS CATALYST

KW - METAL-COMPLEXES

KW - CYCLOPENTADIENE

KW - SUPPORT

U2 - 10.1039/c3gc41378k

DO - 10.1039/c3gc41378k

M3 - Article

SN - 1463-9262

VL - 16

SP - 1470

EP - 1479

JO - Green Chemistry

JF - Green Chemistry

IS - 3

ER -

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

Abstract

Keywords

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