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Enantioselective Epoxidation of Alkenes by Jacobsen Catalyst Anchored onto Aminopropyl-functionalised Laponite, MCM-41 and FSM-16

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Abstract

The Jacobsen catalyst derivative, (R,R)-[Mn(3,5-dtButsalhd)]ClO4–CAT 2, was immobilized through axial coordination of the metal center onto a Laponite, MCM-41 and FSM-16 functionalized with 3-aminopropyltriethoxysilane. The catalytic activity of the Mn-based materials was screened for the enantioselective epoxidation of three olefins: styrene, α-methylstyrene and 6-CN-2,2′-dimethychromene, using m-CPBA/NMO as oxidant, and the results were compared with the corresponding homogenous complex (CAT 2) and with the Jacobsen’s catalyst, (R,R)-[Mn(3,5-dtButsalhd)Cl]–CAT 1. The results indicate that under comparable condition, the Laponite-based materials show both, higher epoxide yield and enantiomeric excess (ee%) compared to MCM-41 and FSM-16-based materials. The best ee% value was obtained for the substrate 6-CN-2,2′-dimethylchromene (64%) which is very close to that obtained with CAT 2 (67%) in homogeneous phase; for the two regular mesoporous materials (MCM-41 and FSM-16) the catalytic results were more favorable for the FSM-16 samples.

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Acknowledgments

This work was funded by FCT Fundação para a Ciência e a Tecnologia (FCT) and FEDER, through the project ref. POCI/CTM/56192/2004. PD thanks FCT for a Post-Doctoral fellowship. Thanks are due to Dr. Shinji Inagaki, from Toyota Central R&D Labs for the FSM-16 sample.

Author information

Author notes

  1. Pankaj Das

    Present address: Department of Chemistry, Dibrugarh University, Dibrugarh, Assam, 786 004, India

  2. Ana Rosa Silva

    Present address: Unilever R&D, Port Sunlight, Bebington, UK

Authors and Affiliations

  1. REQUIMTE/Departamento de Química, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre, 4169-007, Porto, Portugal

    Pankaj Das, Ana Rosa Silva & Cristina Freire

  2. Departamento de Química e Bioquímica and CQB, Faculdade de Ciências, Universidade de Lisboa, Ed. C8, Campo Grande, 1749-016, Lisbon, Portugal

    Ana P. Carvalho & João Pires

Authors
  1. Pankaj Das
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  2. Ana Rosa Silva
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  3. Ana P. Carvalho
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  4. João Pires
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  5. Cristina Freire
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Correspondence to Cristina Freire.

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Das, P., Silva, A.R., Carvalho, A.P. et al. Enantioselective Epoxidation of Alkenes by Jacobsen Catalyst Anchored onto Aminopropyl-functionalised Laponite, MCM-41 and FSM-16. Catal Lett 129, 367–375 (2009). https://doi.org/10.1007/s10562-008-9793-x

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  • DOI: https://doi.org/10.1007/s10562-008-9793-x

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