Synthesis of novel class of 2-oxazolidinone based chiral ionic liquids

References

• Walden, P. Ueber Die Molekulargrösse Und Elektrische Leitfähigkeit Einiger Geschmolzenen Salze. Bull. Acad. Imper. Sci. St. Petersburg. 1914, 8, 405–422.
   Google Scholar
• (a) Diaw, M.; Chagnes, A.; Carre, B.; Willmann, P.; Lemordant, D. Mixed Ionic Liquid as Electrolyte for Lithium Batteries. J. Power Sources. 2005, 146, 682–684. (b) Wilkes, J. S.; Levisky, J. A.; Wilson, R. A.; Hussey, C. L. Dialkylimidazolium Chloroaluminate Melts: A New Class of Room-Temperature Ionic Liquids for Electrochemistry, Spectroscopy and Synthesis. Inorg. Chem. 1982, 21, 1263–1264. DOI: 10.1016/j.jpowsour.2005.03.068.
   Web of Science ®Google Scholar
• (a) Luo, S.; Cheng, J. P. Functionalized Chiral Ionic Liquids as Highly Efficient Asymmetric Organocatalysts for Michael Addition to Nitroolefins. Angew. Chem. Int. Ed. 2006, 45, 3093–3097. (b) Katharina, B.; Peter, G. Applications of Chiral Ionic Liquids. Eur. J. Org. Chem. 2008, 3235–3250. (c) González, L.; Escorihuela, J.; Altava, B.; Burguete, M. I.; Luis, S. V. Chiral Room Temperature Ionic Liquids as Enantioselective Promoters for the Asymmetric Aldol Reaction. Eur. J. Org. Chem. 2014, 5356. (d) Beltrán, A.; Burguete, M. I.; Abánades, D. R.; Pérez-Sala, D.; Luis, S. V.; Galindo, F. Turn-on Fluorescent Probes for Nitric Oxide Sensing Based on the Ortho-Hydroxyamino Structure Showing No Interference with Dehydroascorbic Acid. Chem. Commun. 2014, 50, 3579–3581. (e) Payra, S.; Saha, A.; S. Chiral Ionic Liquids: Synthesis and Role as Efficient Green Catalyst in Asymmetric Synthesis. Curr. Organocatal. 2017, 4, 4–32. DOI: 10.1002/anie.200600048.
   PubMed Web of Science ®Google Scholar
• (a) David, K. B.; Hadi, M. M.; Fernand, V. E.; Fakayode, S. O.; Lowry, M.; Ioan, N.; Robert, M. S.; Isiah, M. W. Synthesis and Characterization of Novel Chiral Ionic Liquids and Investigation of Their Enantiomeric Recognition Properties. Chirality. 2008, 20, 151–158. (b) Bwambok, D. K.; Marwani, H. M.; Fernand, V. E.; Fakayode, S. O.; Lowry, M.; Negulescu, I.; Strongin, R. M.; Warner, I. M. Synthesis of Chiral Room Temperature Ionic Liquids from Amino Acids – Application in Chiral Molecular Recognition. Eur. J. Org. Chem. 2008, 20, 151–5009.
   PubMed Web of Science ®Google Scholar
• (a) Ding, J.; Welton, T.; Armstrong, D. W. Chiral Ionic Liquids as Stationary Phases in Gas Chromatography. Anal. Chem. 2004, 76, 6819–6822. (b) Biedron, T.; Kubisa, P. Ionic Liquids as Reaction Media for Polymerization Processes: Atom Transfer Radical Polymerization (ATRP) of Acrylates in Ionic Liquids. Polym. Int. 2003, 52, 1584–1588. (c) Biedron, T.; Kubisa, P. J. Radical Polymerization in a Chiral Ionic Liquid: Atom Transfer Radical Polymerization of Acrylates. Polym. Chem. 2005, 43, 3454–3459. (d) Pegot, B.; Vo-Thanh, G.; Loupy, A. Tetrahedron Lett. 2004, 45, 6425–6428. DOI: 10.1021/ac049144c.
   PubMed Web of Science ®Google Scholar
• Miao, W.; Chan, T. H. Ionic-Liquid-Supported Organocatalyst: Efficient and Recyclable Ionic-Liquid-Anchored Proline for Asymmetric Aldol Reaction. Adv. Synth. Catal. 2006, 348, 1711–1718. DOI: 10.1002/adsc.200606059.
   Web of Science ®Google Scholar
• Ou, W. H.; Huang, Z. Z. An Efficient and Practical Synthesis of Chiral Imidazolium Ionic Liquids and Their Application in an Enantioselective Michael Reaction. Green Chem. 2006, 8, 731–735. DOI: 10.1039/b604801c.
   Web of Science ®Google Scholar
• Jodry, J. J.; Mikami, K. New Chiral Imidazolium Ionic Liquids: 3D-Network of Hydrogen Bonding. Tetrahedron Lett. 2004, 45, 4429–4431. DOI: 10.1016/j.tetlet.2004.04.063.
   Web of Science ®Google Scholar
• Luo, S. P.; Xu, D. Q.; Yue, H. D.; Wang, L. P.; Yang, W. L.; Xu, Z. Y. Synthesis and Properties of Novel Chiral-Amine-Functionalized Ionic Liquids. Tetrahedron: Asymmetry. 2006, 17, 2028–2033. DOI: 10.1016/j.tetasy.2006.07.018.
   Google Scholar
• Ni, B.; Headley, A. D. Novel Imidazolium Chiral Ionic Liquids That Contain a Urea Functionality. Tetrahedron Lett. 2006, 47, 7331. DOI: 10.1016/j.tetlet.2006.08.015.
   Web of Science ®Google Scholar
• Ni, B.; Zhang, Q.; Headley, A. Functionalized Chiral Ionic Liquid as Efficient Organocatalyst for Asymmetric Michael Addition to Nitroalkenes. Green Chem. 2007, 9, 737–739. DOI: 10.1039/b702081c.
   Web of Science ®Google Scholar
• (a) Heravi, M. M.; Zadsirjan, V.; Farajpour, B. Applications of Oxazolidinones as Chiral Auxiliaries in the Asymmetric Alkylation Reaction Applied to Total Synthesis. RSC Adv. 2016, 6, 30498–30551. (b) Isart, C.; Burés, J.; Vilarrasa, J. Seebach’s Oxazolidinone Is a Good Catalyst for Aldol Reactions. Tetrahedron Lett. 2008, 49, 5414–5418. DOI: 10.1039/C6RA00653A.
   Web of Science ®Google Scholar
• Dickman, M.; Jones, J. B. Covalent Modification of Subtilisin Bacillus lentus Cysteine Mutants with Enantiomerically Pure Chiral Auxiliaries Causes Remarkable Changes in Activity. Bioorg. Med. Chem. 2000, 8, 1957–1968. DOI: 10.1016/S0968-0896(00)00121-8.
   PubMed Web of Science ®Google Scholar
• Allan, D.; Headley, B. Ni, Chiral Imidazolium Ionic Liquids: Their Synthesis and Influence on the Outcome of Organic Reactions. Aldrichimica Acta. 2007, 40.
   Web of Science ®Google Scholar