Synthesis and characterization of novel chiral imidazolium and pyridinium ionic liquids derived from tartaric acid and 2-oxazolidinone

References

• Lewandowski, A.; Galiński, M. Carbon-Ionic Liquid Double-Layer Capacitors. J. Phys. Chem. Sol. 2004, 65, 281-286. DOI: 10.1016/j.jpcs.2003.09.009.
   Web of Science ®Google Scholar
• Walden, P.; Die, U. Molekulargrösse and Elektrische Leitfähigkeit Einiger Geschmolzenen Salze. Bull. Acad. Imper. Sci. St. Petersburg 1914, 8, 405-422.
   Google Scholar
• (a) Bwambok, D. K., Marwani, H. M.; Fernand, V. E.; Fakayode, S. O.; Lowry, M.; Negulescu, I.; Strongin, R. M.; Warner, I. M.. Synthesis and Characterization of Novel Chiral Ionic Liquids and Investigation of their Enantiomeric Recognition Properties. Chirality 2008, 20, 151-158. DOI: 10.1002/chir.20517.
   PubMed Web of Science ®Google Scholar
  (b) Laura, G.; Belén, A.; Michael, B.; Isabel, B.; Eduardo, G. ‐V.; Santiago, V. L. Synthesis of Chiral Room Temperature Ionic Liquids from Amino Acids - Application in Chiral Molecular Recognition. Eur. J. Org. Chem. 2012, 4996-5009. DOI: 10.1002/ejoc.201200607.
   Web of Science ®Google Scholar
  (c) Ding, J.; Welton, T.; Armstrong, D. W. Chiral Ionic Liquids as Stationary Phases in Gas Chromatography. Anal. Chem. 2004, 76, 6819-6822. DOI: 10.1021/ac049144c.
   PubMed Web of Science ®Google Scholar
• (a) 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, 2014, 5356. DOI: 10.1002/ejoc.201402436.
   Web of Science ®Google Scholar
  (b)Beltrán, A.; Isabel Burguete, M.; Abánades, D. R.; Pérez-Sala, D.; Luis, S. V.; Galindo, F. Luis and Francisco Galindo. 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. DOI: 10.1039/C3CC49555H.
   PubMed Web of Science ®Google Scholar
  (c) Soumen, P.; Arijit, S.; Subhash, B. Chiral Ionic Liquids: Synthesis and Role as Efficient Green Catalyst in Asymmetric Synthesis. Curr. Organocatal. 2017, 4, 4-32. DOI: 10.2174/2213337203666160524143221.
   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
• (a) Buskens, P.; Klankermayer, J.; Leitner, W. Bifunctional Activation and Racemization in the Catalytic Asymmetric Aza-Baylis-Hillman Reaction. J. Am. Chem. Soc. 2005, 127, 16762-16763. DOI: 10.1021/ja0550024.
   PubMed Web of Science ®Google Scholar
  (b) Gausepohl, R.; Buskens, P.; Kleinen, J.; Bruckmann, A.; Lehmann, C. W.; Klankermayer, J.; Leitner, W. Highly Enantioselective aza-Baylis-Hillman Reaction In A Chiral Reaction Medium. Angew. Chem. Int. Ed. Engl. 2006, 45, 3689-3692. DOI: 10.1002/anie.200600327.
   PubMed Web of Science ®Google Scholar
• Fischer, T.; Sethi, A.; Welton, T.; Woolf, J. Diels-Alder Reactions in Room-Temperature Ionic Liquids. Tetrahedron Lett. 1999, 40, 793-796. DOI: 10.1016/S0040-4039(98)02415-0.
   Web of Science ®Google Scholar
• Wang, Z.; Wang, Q.; Zhang, Y.; Bao, W. Synthesis of New Chiral Ionic Liquids from Natural Acids and their Applications in Enantioselective Michael Addition. Tetrahedron Lett. 2005, 46, 4657-4660. DOI: 10.1016/j.tetlet.2005.04.134.
   Web of Science ®Google Scholar
• Geldbach, T. J.; Dyson, P. J. A Versatile Ruthenium Precursor for Biphasic Catalysis and its Application in Ionic Liquid Biphasic Transfer Hydrogenation: Conventional vs Task-Specific Catalysts. J. Am. Chem. Soc. 2004, 126, 8114. DOI: 10.1021/ja048886k.
   PubMed Web of Science ®Google Scholar
• Gadenne, B.; Hesemann, P.; Moreau, J. J. E. Ionic Liquids Incorporating Camphorsulfonamide Units for the Ti-Promoted Asymmetric Diethylzinc Addition to Benzaldehyde. Tetrahedron Lett. 2004, 45, 8157-8160. DOI: 10.1016/j.tetlet.2004.09.038.
   Web of Science ®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. DOI: 10.1016/j.jpowsour.2005.03.068.
   Web of Science ®Google Scholar
  (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: 10.1021/ic00133a078.
   Web of Science ®Google Scholar
• Dal, W.; Li, J.; Chen, B.; Li, G.; Lv, Y.; Wang, L.; Shang, G. Asymmetric Oxidation Catalysis by a Porphyrin-Inspired Manganese Complex: Highly Enantioselective Sulfoxidation with a Wide Substrate Scope. Org. Lett. 2013, 15, 5658. DOI: 10.1021/ol402612x.
   PubMed Web of Science ®Google Scholar
• (a) Pitchen, P.; Kagan, H. B. An Efficient Asymmetric Oxidation of Sulfides to Sulfoxides. Tetrahedron Lett. 1984, 25, 1049. DOI: 10.1016/S0040-4039(01)80097-6.
   Web of Science ®Google Scholar
  (b) Pitchen, P.; Dunach, E.; Deshmukh, M. N.; Kagan, H. B. An Efficient Asymmetric Oxidation of Sulfides to Sulfoxides. J. Am. Chem. Soc. 1984, 106, 8188. DOI: 10.1021/ja00338a030.
   Web of Science ®Google Scholar
• Di Furia, F.; Modena, G. Seraglia, R. A New Synthesis of Diaryl Sulfones. Synthesis 1984, 4, 323-325. DOI: 10.1055/s-1984-30828.
   Google Scholar
• Katsuki, T.; Sharpless, K. B. The first practical method for asymmetric epoxidation. J. Am. Chem. Soc 1980, 102, 5974. DOI: 10.1021/ja00538a077.
   Web of Science ®Google Scholar
• Nehate, S. P.; Godbole, H. M.; Singh, G. P.; Jessy E, M.; Gautham G, S. Synthesis of Novel Class of 2-oxazolidinone Based Chiral Ionic Liquids. Synth. Comm. 2018, 48, 2435-2440. DOI: 10.1080/00397911.2018.1496260.
   Web of Science ®Google Scholar
• (a) Machado, M. Y.; Dorta, R. Synthesis and Characterization of Chiral Imidazolium Salts. Synthesis 2005, 15, 2473. DOI: 10.1055/s-2005-872102.
   Web of Science ®Google Scholar
  (b) Wang, Z.; Wang, Q.; Zhang, Y.; Bao, W. Synthesis of New Chiral Ionic Liquids from Natural Acids and Their Applications in Enantioselective Michael Addition. Tetrahedron Lett. 2005, 46, 4657. DOI: 10.1016/j.tetlet.2005.04.134.
   Web of Science ®Google Scholar