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2009 | 11 | 3 | 8-14
Article title

One-pot synthesis of (S)-2-(6-methoxynaphtalen-2-yl)propanoic acid, (S)-Naproxen using Preyssler and Keggin-type heteropolyacids as green and reusable catalysts

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EN
Abstracts
EN
A simple, clean and environmentally benign route to the enantioselective synthesis of (S)-2-(6-methoxynaphtalen-2-yl)propanoic acid, (S)-Naproxen 3 is described by using Preyssler heteropolyacid, H14[NaP5W30O110], as a green and reusable catalyst in water and in the presence of 1-(6-methoxynaphthalen-2-yl)propan-1-one 1, D-mannitol 2. The products were obtained in very good yields.
Publisher

Year
Volume
11
Issue
3
Pages
8-14
Physical description
Dates
published
1 - 1 - 2009
online
9 - 10 - 2009
Contributors
author
  • School of Pharmacy, Memorial University of Newfoundland, St. John's, Newfoundland, Canada A1C 3V6
author
  • Cluster for Molecular Chemistry, Department of Organic Chemistry, Radboud University Nijmegen, The Netherlands
  • Department of Chemistry, School of Science, Islamic Azad University, Mashhad, IRAN
author
  • Department of Chemistry, School of Science, Islamic Azad University, Mashhad, IRAN
  • Department of Chemistry, School of Science, Islamic Azad University, Mashhad, IRAN
References
  • Izumi, Y., Urabe, K. & Onaka, M. (1992). Zeolite, Clay and Heteropoly Acid in Organic Reactions, Kodansha/VCH, Tokyo.
  • Okuhara, T., Mizuno, N. & Misono, M. (1996). Advances in Catalysis. Catalytic Chemistry of Heteropoly compounds. 41, 113-252.
  • Kozhevnikov, I. V. (1998). Catalysis by Heteropoly Acids and Multicomponent Polyoxometalates in Liquid-Phase Reactions. Chem. Rev. 98, 171-198. DOI: 10.1021/cr960400y[Crossref]
  • Kozhevnikov, I. V. (2002). Catalysts for fine chemicals, in: Catalysis by Polyoxometalates, vol. 2, Wiley, Chichester.
  • Moffat, J. B. (2001). Metal-Oxygen Clusters. The Surface and Catalytic Properties of Heteropoly Oxometalates, Kluwer Academic Publishers, New York.
  • Oreste, P., Franca, S. & Giuseppina, V. (1987). Zinc salt catalyzed rearrangement of acetals of optically active aryl 1-chloroethyl ketones: synthesis of optically active 2-arylpropionic acids and esters. J. Org. Chem. 52, 10-14. DOI: 10.1021/jo00377a002.[Crossref]
  • Saunders, M., Chandrasekhar, J. & Schleyer, P. V. R. (1980). Rearrangements in Ground and Excited States, Academic Press.
  • Barner, B. A. & Kurland, J. J. (1997). WO 9714669A1.
  • Fan, Q. H., Chen, Y. M., Chen, X. M., Jiang, D. Z., Xi, F. & Chan, A. S. C. (2000). Highly effective and recyclable dendritic BINAP ligands for asymmetric hydrogenation. Chem. Commun. 789-790. DOI: 10.1039/b001503m.[Crossref]
  • Ward, J. Borner, A. & Kagan, H. B. (1992). Synthesis of 6-endo-hydroxy norphos, a potential ligand for construction of chiral bimetallic catalysts. Tetrahedron: Asymmetry. 3, 849-852. DOI:10.1016/S0957-4166(00)82181-3.[Crossref]
  • Schmidt, R., Foricher, J., Cereghetti, M. & Schonholzer, P. (1991). Axially Dissymmetric Diphosphines in the Biphenyl Series: Synthesis of (6,6 -Dimethoxybiphenyl- 2,2 -diyl)bis(diphenylphosphine)(MeO-BIPHEP) and Analogues via an ortho-Lithiation/Iodination Ullmann-Reaction Approach. Helv. Chem. Acta.74, 370-389. DOI: 10.1002/hlca.19910740215.[Crossref]
  • Bamoharram, F. F., Heravi, M. M., Roshani, M., Jahangir, M. & Gharib, A. (2007). Effective direct esterification of butanol by eco-friendly Preyssler catalyst, [NaP5W30O110]14-. J. Mol. Catal. 271, 126-130. DOI:10.1016/j.molcata.2007.02.034.[Crossref][WoS]
  • Bamoharram, F. F., Heravi, M. M., Roshani, M., Jahangir, M. & Gharib, A. (2006). Preyssler catalyst, [NaP5W30O110]14-: A green, efficient and reusable catalyst for esterification of salicylic acid with aliphatic and benzylic alcohols. Applied Catalysis A: General. 302, 42-47. DOI:10.1016/j.apcata.2005.12.021.[Crossref]
  • Heravi, M. M., Bakhtiari, K., Benmorad, T., Bamoharram, F. F., Heravi, M. M., Oskooie, H. A., & Tehrani, H. M (2007). Nitration of Aromatic Compounds Catalyzed by Divanadium-Substituted Molybdophosphoric Acid, H5[PMo10V2O40]. Monatshefte für Chemie. 138, 5, 449-452. DOI: 10.1007/s00706-007-0593-6.[WoS][Crossref]
  • Hill, C. L. (1989). Catalytic Oxygenation of Unactivated C-H Bonds. Superior Oxo Transfer Catalysts and the Inorganic Porphyrin'. In Activation and Functionalization of Alkanes., Ed., Wiley: New York, pp 243-279.
  • Bamoharram, F. F., Heravi, M. M., Roshani, M., Gharib, A. & Jahangir, M. (2006). A catalytic method for synthesis of γ-butyrolactone, ε-caprolactone and 2-cumaranone in the presence of Preyssler's anion, [NaP5W30O110]14-, as a green and reusable catalyst. J. Mol. Catal. 252, 90-95. DOI:10.1016/j.molcata.2006.01.067.[Crossref]
  • Alper, H. & Hamel, H. (1990). Asymmetric synthesis of acids by the palladium-catalyzed hydrocarboxylation of olefins in the presence of (R)-(-)- or (S)-(+)-1,1'-binaphthyl- 2,2'-diyl hydrogen phosphate. J. Am. Chem. Soc. 112, 2803-2804. DOI: 10.1021/ja00163a053.[Crossref]
  • Romanelli, G., Autino, J. C., Baronetti, G. & Thomas, H. (2001). H. Efficient Deprotection of Phenol Methoxymethyl Ethers Using a Solid Acid Catalyst with Wells-Dawson Structure. Molecules. 6, 1006-1011. DOI:10.3390/61201006.[Crossref]
Document Type
Publication order reference
Identifiers
YADDA identifier
bwmeta1.element.-psjd-doi-10_2478_v10026-009-0029-7
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