Asymmetric carbon-carbon bond forming reactions catalysed by metal(II) bis(oxazoline) complexes immobilized using supported ionic liquids

P. Goodrich; C. Hardacre; C. Paun; A. Ribeiro; S. Kennedy; M. J V Lourenço; H. Manyar; C. A Nieto De Castro; M. Besnea; V. I. Pârvulescu

doi:10.1002/adsc.201000953

Asymmetric carbon-carbon bond forming reactions catalysed by metal(II) bis(oxazoline) complexes immobilized using supported ionic liquids

P. Goodrich, C. Hardacre^*, C. Paun, A. Ribeiro, S. Kennedy, M. J V Lourenço, H. Manyar, C. A Nieto De Castro, M. Besnea, V. I. Pârvulescu

^*Corresponding author for this work

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

Abstract

A series of bis(oxazoline) metal(II) complexes has been supported on silica and carbon supports by non-covalent immobilisation using an ionic liquid. The catalytic performance of these solids was compared for the enantioselective Diels-Alder reaction between N-acryloyloxazolidinone and cyclopentadiene and the Mukaiyama-aldol reaction between methyl pyruvate and 1-methoxy-1- trimethylsilyloxypropene. In both reactions the enantioselectivity was strongly influenced by the choice of support displaying enantioselectivies (ee values) up to 40% higher than those conducted under homogeneous reaction conditions.

Original language	English
Pages (from-to)	995-1004
Number of pages	10
Journal	Advanced synthesis & catalysis
Volume	353
Issue number	6
DOIs	https://doi.org/10.1002/adsc.201000953
Publication status	Published - 18 Apr 2011

Keywords

asymmetric catalysis
Diels-Alder reaction
ionic liquids
Mukaiyama-aldol reaction
supported catalysts

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10.1002/adsc.201000953

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Goodrich, P., Hardacre, C., Paun, C., Ribeiro, A., Kennedy, S., Lourenço, M. J. V., Manyar, H., De Castro, C. A. N., Besnea, M., & Pârvulescu, V. I. (2011). Asymmetric carbon-carbon bond forming reactions catalysed by metal(II) bis(oxazoline) complexes immobilized using supported ionic liquids. Advanced synthesis & catalysis, 353(6), 995-1004. https://doi.org/10.1002/adsc.201000953

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title = "Asymmetric carbon-carbon bond forming reactions catalysed by metal(II) bis(oxazoline) complexes immobilized using supported ionic liquids",

abstract = "A series of bis(oxazoline) metal(II) complexes has been supported on silica and carbon supports by non-covalent immobilisation using an ionic liquid. The catalytic performance of these solids was compared for the enantioselective Diels-Alder reaction between N-acryloyloxazolidinone and cyclopentadiene and the Mukaiyama-aldol reaction between methyl pyruvate and 1-methoxy-1- trimethylsilyloxypropene. In both reactions the enantioselectivity was strongly influenced by the choice of support displaying enantioselectivies (ee values) up to 40% higher than those conducted under homogeneous reaction conditions.",

keywords = "asymmetric catalysis, Diels-Alder reaction, ionic liquids, Mukaiyama-aldol reaction, supported catalysts",

author = "P. Goodrich and C. Hardacre and C. Paun and A. Ribeiro and S. Kennedy and Louren{\c c}o, {M. J V} and H. Manyar and {De Castro}, {C. A Nieto} and M. Besnea and P{\^a}rvulescu, {V. I.}",

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doi = "10.1002/adsc.201000953",

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Goodrich, P, Hardacre, C, Paun, C, Ribeiro, A, Kennedy, S, Lourenço, MJV, Manyar, H, De Castro, CAN, Besnea, M & Pârvulescu, VI 2011, 'Asymmetric carbon-carbon bond forming reactions catalysed by metal(II) bis(oxazoline) complexes immobilized using supported ionic liquids', Advanced synthesis & catalysis, vol. 353, no. 6, pp. 995-1004. https://doi.org/10.1002/adsc.201000953

TY - JOUR

T1 - Asymmetric carbon-carbon bond forming reactions catalysed by metal(II) bis(oxazoline) complexes immobilized using supported ionic liquids

AU - Goodrich, P.

AU - Hardacre, C.

AU - Paun, C.

AU - Ribeiro, A.

AU - Kennedy, S.

AU - Lourenço, M. J V

AU - Manyar, H.

AU - De Castro, C. A Nieto

AU - Besnea, M.

AU - Pârvulescu, V. I.

PY - 2011/4/18

Y1 - 2011/4/18

N2 - A series of bis(oxazoline) metal(II) complexes has been supported on silica and carbon supports by non-covalent immobilisation using an ionic liquid. The catalytic performance of these solids was compared for the enantioselective Diels-Alder reaction between N-acryloyloxazolidinone and cyclopentadiene and the Mukaiyama-aldol reaction between methyl pyruvate and 1-methoxy-1- trimethylsilyloxypropene. In both reactions the enantioselectivity was strongly influenced by the choice of support displaying enantioselectivies (ee values) up to 40% higher than those conducted under homogeneous reaction conditions.

AB - A series of bis(oxazoline) metal(II) complexes has been supported on silica and carbon supports by non-covalent immobilisation using an ionic liquid. The catalytic performance of these solids was compared for the enantioselective Diels-Alder reaction between N-acryloyloxazolidinone and cyclopentadiene and the Mukaiyama-aldol reaction between methyl pyruvate and 1-methoxy-1- trimethylsilyloxypropene. In both reactions the enantioselectivity was strongly influenced by the choice of support displaying enantioselectivies (ee values) up to 40% higher than those conducted under homogeneous reaction conditions.

KW - asymmetric catalysis

KW - Diels-Alder reaction

KW - ionic liquids

KW - Mukaiyama-aldol reaction

KW - supported catalysts

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U2 - 10.1002/adsc.201000953

DO - 10.1002/adsc.201000953

M3 - Article

AN - SCOPUS:79955448441

SN - 1615-4150

VL - 353

SP - 995

EP - 1004

JO - Advanced synthesis & catalysis

JF - Advanced synthesis & catalysis

IS - 6

ER -

Asymmetric carbon-carbon bond forming reactions catalysed by metal(II) bis(oxazoline) complexes immobilized using supported ionic liquids

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