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. Lourenco; H. Manyar; C.A.N. De Castro; M. Besnea; V.I. Parvulescu

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. Lourenco, H. Manyar, C.A.N. De Castro, M. Besnea, V.I. Parvulescu

School of Chemistry and Chemical Engineering

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

27 Citations (Scopus)

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-trimethylsilyloxy-propene. 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

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.201000953

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Goodrich, P., Hardacre, C., Paun, C., Ribeiro, A., Kennedy, S., Lourenco, M. J. V., Manyar, H., De Castro, C. A. N., Besnea, M., & Parvulescu, 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-trimethylsilyloxy-propene. 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.",

author = "P. Goodrich and C. Hardacre and C. Paun and A. Ribeiro and S. Kennedy and M.J.V. Lourenco and H. Manyar and {De Castro}, C.A.N. and M. Besnea and V.I. Parvulescu",

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doi = "10.1002/adsc.201000953",

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Goodrich, P, Hardacre, C, Paun, C, Ribeiro, A, Kennedy, S, Lourenco, MJV, Manyar, H, De Castro, CAN, Besnea, M & Parvulescu, 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 - Lourenco, M.J.V.

AU - Manyar, H.

AU - De Castro, C.A.N.

AU - Besnea, M.

AU - Parvulescu, 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-trimethylsilyloxy-propene. 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-trimethylsilyloxy-propene. 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.

U2 - 10.1002/adsc.201000953

DO - 10.1002/adsc.201000953

M3 - Article

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

Abstract

ASJC Scopus subject areas

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