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Journal articles on the topic 'Chiral ionic liquids'

Author: Grafiati

Published: 4 June 2021

Last updated: 15 February 2022

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1

Nobuoka, Kaoru, Satoshi Kitaoka, Tsutomu Kojima, Yuuki Kawano, Kazuya Hirano, Masakazu Tange, Shunsuke Obata, Yuki Yamamoto, Thomas Harran, and Yuich Ishikawa. "Proline Based Chiral Ionic Liquids for Enantioselective Michael Reaction." Organic Chemistry International 2014 (November 20, 2014): 1–9. http://dx.doi.org/10.1155/2014/836126.

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Chiral ionic liquids, starting from (S)-proline, have been prepared and evaluated the ability of a chiral catalyst. In Michael reaction of trans-β-nitrostyrene and cyclohexanone, all the reactions were carried out under homogeneous conditions without any solvent except for excess cyclohexanone. The chiral ionic liquid catalyst with the positive charge delocalized bulky pyrrolidinium cation shows excellent yields (up to 92%), diastereoselectivities (syn/anti = 96/4), and enantioselectivities (up to 95% ee) and could be reused at least three times without any loss of its catalytic activity. Such results demonstrated a promising new approach for green and economic chiral synthesis by using the chiral ionic liquids as a chiral catalyst and a chiral medium.

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2

Flieger, Jolanta, Joanna Feder-Kubis, and Małgorzata Tatarczak-Michalewska. "Chiral Ionic Liquids: Structural Diversity, Properties and Applications in Selected Separation Techniques." International Journal of Molecular Sciences 21, no. 12 (June 15, 2020): 4253. http://dx.doi.org/10.3390/ijms21124253.

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Ionic liquids (ILs) are chemical compounds composed of ions with melting points below 100 °C exhibiting a design feature. ILs are commonly used as the so-called green solvents, reagents or highly efficient catalysts in varied chemical processes. The huge application potential of ionic liquids (IL) justifies the growing interest in these compounds. In the last decade, increasing attention has been devoted to the development of new methods in the synthesis of stable chiral ionic liquids (CILs) and their application in various separation techniques. The beginnings of the successful use of CILs to separate enantiomers date back to the 1990 s. Most chiral ILs are based on chiral cations or chiral anions. There is also a limited number of CILs possessing both a chiral cation and a chiral anion. Due to the high molecular diversity of both ions, of which at least one has a chiral center, we have the possibility to design a large variety of optically active structures, thus expanding the range of CIL applications. Research utilizing chiral ionic liquids only recently has become more popular. However, it is the area that still has great potential for future development. This review aimed to describe the diversity of structures, properties and examples of applications of chiral ionic liquids as new chiral solid materials and chiral components of the anisotropic environment, providing chiral recognition of enantiomeric analytes, which is useful in liquid chromatography, countercurrent chromatography and other various CIL-based extraction techniques including aqueous biphasic (ABS) extraction systems, solid–liquid two-phase systems, liquid–liquid extraction systems with hydrophilic CILs, liquid–liquid extraction systems with hydrophobic CILs, solid-phase extraction and induced-precipitation techniques developed in the recent years. The growing demand for pure enantiomers in the pharmaceutical and food industries sparks further development in the field of extraction and separation systems modified with CILs highlighting them as affordable and environmentally friendly both chiral selectors and solvents.

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3

Vasiloiu, Maria, Sonja Leder, Peter Gaertner, Kurt Mereiter, and Katharina Bica. "Coordinating chiral ionic liquids." Organic & Biomolecular Chemistry 11, no. 46 (2013): 8092. http://dx.doi.org/10.1039/c3ob41635f.

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4

Lauth-de Viguerie, Nancy, Cosmin Patrascu, Claudia Sugisaki, Christophe Mingotaud, Jean-Daniel Marty, and Yves Génisson. "New Pyridinium Chiral Ionic Liquids." HETEROCYCLES 63, no. 9 (2004): 2033. http://dx.doi.org/10.3987/com-04-10133.

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5

Zalewska, Karolina, and Luis C. Branco. "Organocatalysis with Chiral Ionic Liquids." Mini-Reviews in Organic Chemistry 11, no. 2 (June 2014): 141–53. http://dx.doi.org/10.2174/1570193x1102140609120011.

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6

Bica, Katharina, and Peter Gaertner. "Applications of Chiral Ionic Liquids." European Journal of Organic Chemistry 2008, no. 19 (July 2008): 3235–50. http://dx.doi.org/10.1002/ejoc.200701107.

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7

Ahn, Sangbum, Shohei Yamakawa, and Kazuo Akagi. "Liquid crystallinity-embodied imidazolium-based ionic liquids and their chiral mesophases induced by axially chiral tetra-substituted binaphthyl derivatives." Journal of Materials Chemistry C 3, no. 16 (2015): 3960–70. http://dx.doi.org/10.1039/c4tc02968b.

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The novel liquid crystalline ionic liquids (LCILs) were synthesised by introducing LC chains into both sides of imidazolium derivatives. The LCILs exhibited chiral nematic (N*) phases when the chiral dopants were added to the LCILs.

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8

Singh, Avtar, Nirmaljeet Kaur, and Harish Kumar Chopra. "Enantioselective Reduction Reactions Using Chiral Ionic Liquids: An Overview." Current Organic Synthesis 15, no. 5 (July 5, 2018): 578–86. http://dx.doi.org/10.2174/1570179415666180427111428.

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Background: Enantioselective reduction reactions play a key role to synthesize compounds of industrial importance. A number of metal and biocatalysts have been developed for their use in this reaction. Chiral ionic liquids (CILs) have been widely used as the reaction medium and the organocatalysts in enantioselective reduction reactions. Objective: This paper focuses on the systematic literature review about the use of chiral ionic liquids (CILs) in the enantioselective reduction reaction. The mechanistic aspects of these species are also taken into account. Conclusion: This review concludes that a number of chiral ionic liquids (CILs) have been successfully employed as the organocatalysts and the reaction medium in the enantioselective reduction reactions. The review also gives an insight into the role of these species in the reaction mechanism. For most of the reactions, chiral ionic liquids provide promising results in terms of yield and enantioselectivity. The recyclability of these chiral moieties from the reaction mixtures offers an additional benefit for the use of these species in asymmetric reactions.

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9

Wang, Hong Li, Xiao Ling Hu, Ping Guan, Jin Yang Yu, and Yi Mei Tang. "Synthesis and Characterization of Novel Ester Functionalized Chiral Ionic Liquids." Advanced Materials Research 197-198 (February 2011): 471–77. http://dx.doi.org/10.4028/www.scientific.net/amr.197-198.471.

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Three different chiral ionic liquids, chloride (R)-(+)-β-(1-methyl-imidazole)–propio-nate, (R)-(+)-β-(1-methyl-imidazole)-propionate terafluoroborate and hexafluorophosphate, weresuccessfully synthesized via the nucleophilic substitution reaction and the anion metathesis reaction, with (S)-(-)-2-chloro-propionic acid as the chiral source. Structures of the chiral io-nic liquids have been characterized by the infrared spectroscopy, nuclear magnetic resonancespectroscopy and quantum chemical structure optimization method. These new ionic materia-ls can be used as building blocks for the synthesis of ionic liquids.

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10

Marwani, Hadi. "Spectroscopic evaluation of chiral and achiral fluorescent ionic liquids." Open Chemistry 8, no. 4 (August 1, 2010): 946–52. http://dx.doi.org/10.2478/s11532-010-0062-7.

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AbstractIn this study, spectroscopic investigation of chiral and achiral room temperature ionic liquids is achieved. New ionic liquids were prepared via metathesis, accomplished by the reaction of either L-phenylalanine ethyl ester hydrochloride, chlorpromazine hydrochloride or 1,10-Phenanthroline monohydrate hydrochloride with lithium bis(trifluoromethane) sulfonamide in water. The resulting ionic liquids were produced in high yield and purity. The results obtained by use of 1H NMR and IR experiments were in very good agreement with the chemical structures of the synthesized ionic liquids. In addition, the results of thermal gravimetric analysis suggested that these ionic liquids have good thermal stability. UV-Vis and fluorescence spectroscopy measurements indicated that these ionic liquids are strongly optically absorbent and fluorescent. Lastly, time-based fluorescence steady-state measurements demonstrated the high photostability of these ionic liquids.

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11

Schulz, Peter S., Karola Schneiders, and Peter Wasserscheid. "Aggregation behaviour of chiral ionic liquids." Tetrahedron: Asymmetry 20, no. 21 (November 2009): 2479–81. http://dx.doi.org/10.1016/j.tetasy.2009.10.010.

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12

Pastrán, Jesús, Giuseppe Agrifoglio, Teresa González, Alexander Briceño, and Romano Dorta. "Camphorpyrazolium-based chiral functional ionic liquids." Tetrahedron: Asymmetry 25, no. 18-19 (October 2014): 1280–85. http://dx.doi.org/10.1016/j.tetasy.2014.07.014.

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13

Singh, Gurdial, Patrice Plaza, and Bhoomendra Bhongade. "Synthesis of Chiral Carbohydrate Ionic Liquids." Synlett 2009, no. 02 (January 15, 2009): 332–0332. http://dx.doi.org/10.1055/s-0028-1087525.

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14

Glushkov, V. A., M. S. Kotelev, K. S. Rudovskii, O. A. Maiorova, A. V. Tarantin, and A. G. Tolstikov. "Chiral ionic liquids based on abietane." Russian Journal of Organic Chemistry 45, no. 3 (March 2009): 404–7. http://dx.doi.org/10.1134/s1070428009030099.

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15

Singh, Gurdial, Patrice Plaza, and Bhoomendra Bhongade. "Synthesis of Chiral Carbohydrate Ionic Liquids." Synlett 2008, no. 19 (November 12, 2008): 2973–76. http://dx.doi.org/10.1055/s-0028-1087343.

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16

Ding, Jie, and Daniel W. Armstrong. "Chiral ionic liquids: Synthesis and applications." Chirality 17, no. 5 (2005): 281–92. http://dx.doi.org/10.1002/chir.20153.

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17

Vasiloiu, Maria, Sonja Leder, Peter Gaertner, Kurt Mereiter, and Katharina Bica. "ChemInform Abstract: Coordinating Chiral Ionic Liquids." ChemInform 45, no. 15 (March 27, 2014): no. http://dx.doi.org/10.1002/chin.201415023.

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18

Janus, Ewa, and Marcin Gano. "Chiral pyrrolidinium salts derived from menthol as precursor – synthesis and properties." Polish Journal of Chemical Technology 19, no. 3 (September 1, 2017): 92–98. http://dx.doi.org/10.1515/pjct-2017-0054.

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Abstract Six new chiral pyrolidinium salts with chiral substituent at quaternary nitrogen atom were synthesized with high overall yields from (-)-menthol as cheap chiral precursor and were identified by NMR and HRMS spectroscopy. It was shown that anion type had the effect on chemical shift of protons adjacent to quaternary nitrogen atom and physical properties of these salts. Salts with NTf2 or NPf2 were in a liquid state at room temperature and characterized with the highest thermal stability among others. Furthermore, chiral ionic liquid with NTf2 anion was used as solvent in Diels-Alder reaction and gave higher yield and stereoselectivity than in ionic liquids with achiral cations. Synthesized chiral salts have the potential as chiral solvents in synthesis and auxiliaries in analytical methods to improve chiral recognition.

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19

Bacha, Katia, Kawther Aguibi, Jean-Pierre Mbakidi, and Sandrine Bouquillon. "Beneficial Contribution of Biosourced Ionic Liquids and Microwaves in the Michael Reaction." Catalysts 10, no. 8 (July 22, 2020): 814. http://dx.doi.org/10.3390/catal10080814.

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We developed a synthesis of chiral ionic liquids from proline and one of its derivatives. Nine chiral ionic liquids were synthesized with yields from 78% to 95%. These synthesized ionic liquids played two roles in Michael reactions, as solvents, and as basic catalysts, where the ionic phase could also be reused at least five times without loss of activity. The yields up to 99% were improved by increasing the amount of dimethylmalonate from 1.2 equivalents to 3 or 4 equivalents. Furthermore, the reaction time could be reduced from 24 h to 45 min through microwaves activation.

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20

Brown, Christopher J., and Todd A. Hopkins. "Chiral Discrimination by Ionic Liquids: Impact of Ionic Solutes." Chirality 27, no. 4 (February 26, 2015): 320–25. http://dx.doi.org/10.1002/chir.22435.

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21

Meng, Hong, Sumin Li, Ling Xiao, and Chunxi Li. "Inclusion Phenomena between theβ-Cyclodextrin Chiral Selector and Trp-D,L, and Its Use on the Assembly of Solid Membranes." Journal of Nanomaterials 2013 (2013): 1–8. http://dx.doi.org/10.1155/2013/170913.

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The application ofβ-cyclodextrin (β-CD) and the chiral ionic liquids formed fromβ-cyclodextrin mono-6-deoxy-6-(3-methylimidazolium)-β-cyclodextrin tosylate (β-CD-IL) as chiral selectors is described. The inclusion phenomena between theβ-cyclodextrin chiral selectors and D,L-tryptophan (D,L-Trp) was studied. The inclusion compounds were prepared by grinding, and their properties analyzed by X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), and nuclear magnetic resonance (NMR). The separation factor betweenβ-CD andβ-CD-IL with D,L-Trp was studied by the saturated solution method. This indicated a different binding capacity ofβ-CD andβ-CD-IL to the two enantiomers. This result shows that the chiral ionic liquids have a higher separation factor because of their high solubility. Theβ-cyclodextrin chiral ionic liquids and CS were cross-linked and immobilized on an N6 membrane to form composite membranes. Adsorption experiments and permeation experiments were carried out. 105.43 mg D,L-Trp/g membrane was obtained.

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22

Qian, Li Wei, Xiao Ling Hu, Ping Guan, and Xiao Qing Guo. "Bi-Functional Magnetical Chiral Ionic Liquids Derived from Imidazolium and Pyridinium." Applied Mechanics and Materials 161 (March 2012): 128–33. http://dx.doi.org/10.4028/www.scientific.net/amm.161.128.

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Novel Bi-Functional Magnetical Chiral Ionic Liquids (MCILs) Derived from Imidazolium and Pyridinium Were Synthesized via Simply Two Step Reactions. Optically Active Ionic Liquids Have an Asymmetric Carbon Atom Linked to the Positively Charged Imidazole Ring or Pyridine Ring, while the Magnetical Anion Contains Tetrachloroferrate (FeCl4-), their Properties of Chirality and Magnetism Were Characterized. the Structure of MCILs Would Promise a New Class of Bi-Functional Ionic Liquids.

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23

Ashraf, Syed A., Yingpit Pornputtkul, Leon A. P. Kane-Maguire, and Gordon G. Wallace. "Facile Synthesis of a Chiral Ionic Liquid Derived from 1-Phenylethylamine." Australian Journal of Chemistry 60, no. 1 (2007): 64. http://dx.doi.org/10.1071/ch06384.

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A simple route is described to enantiomerically pure ionic liquids derived from (+)- and (–)-1-phenylethylamine. These very low melting point (–42°C) ionic liquids, containing the bis(trifluoromethylsulfonylimide) anion, possess a wide electrochemical potential window between –2.0 and +2.0 V (versus Ag|AgCl). They show chiral discrimination between the enantiomeric forms of Mosher’s salt, suggesting their potential as media for electrochemical asymmetric syntheses or chiral chromatography.

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24

Palazzo, Ivan, Andrea Mezzetta, Lorenzo Guazzelli, Stefania Sartini, Christian Silvio Pomelli, Wallace O. Parker, and Cinzia Chiappe. "Chiral ionic liquids supported on natural sporopollenin microcapsules." RSC Advances 8, no. 38 (2018): 21174–83. http://dx.doi.org/10.1039/c8ra03455a.

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25

Nageshwar, D., D. Muralimohan Rao, and Palle V. R. Acharyulu. "Terpenes to Ionic Liquids: Synthesis and Characterization of Citronellal-Based Chiral Ionic Liquids." Synthetic Communications 39, no. 18 (August 12, 2009): 3357–68. http://dx.doi.org/10.1080/00397910902768226.

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26

González-Mendoza, Laura, Jorge Escorihuela, Belén Altava, M. Isabel Burguete, and Santiago V. Luis. "Application of optically active chiral bis(imidazolium) salts as potential receptors of chiral dicarboxylate salts of biological relevance." Organic & Biomolecular Chemistry 13, no. 19 (2015): 5450–59. http://dx.doi.org/10.1039/c5ob00348b.

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27

Aloni, Sapir Shekef, Milena Perovic, Michal Weitman, Reut Cohen, Martin Oschatz, and Yitzhak Mastai. "Amino acid-based ionic liquids as precursors for the synthesis of chiral nanoporous carbons." Nanoscale Advances 1, no. 12 (2019): 4981–88. http://dx.doi.org/10.1039/c9na00520j.

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28

Santamarta, Francisco, Miguel Vilas, Emilia Tojo, and Yagamare Fall. "Synthesis and properties of novel chiral imidazolium-based ionic liquids derived from carvone." RSC Advances 6, no. 37 (2016): 31177–80. http://dx.doi.org/10.1039/c6ra00654j.

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29

Pothanagandhi, Nellepalli, Akella Sivaramakrishna, and Kari Vijayakrishna. "Chiral anion-triggered helical poly(ionic liquids)." Polymer Chemistry 8, no. 5 (2017): 918–25. http://dx.doi.org/10.1039/c6py02012g.

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30

Zalewska, Karolina, and Luis C. Branco. "ChemInform Abstract: Organocatalysis with Chiral Ionic Liquids." ChemInform 46, no. 4 (January 2015): no. http://dx.doi.org/10.1002/chin.201504289.

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31

Pomputtkul, Y. "Electrochemistry of Chiral Polyaniline in Ionic Liquids." ECS Proceedings Volumes 2004-24, no. 1 (January 2004): 473–87. http://dx.doi.org/10.1149/200424.0473pv.

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32

Gomes da Silva, M. D. R., and M. Manuela A. Pereira. "New chiral imidazolium ionic liquids from isomannide." Carbohydrate Research 346, no. 2 (February 2011): 197–202. http://dx.doi.org/10.1016/j.carres.2010.11.011.

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33

Zhou, Jie, Suzhen Zhao, Guangjun Fu, and Zhenzhong Zhang. "Isoleucine ionic liquids as additives to separate mandelic acid and their derivative enantiomers by HPLC." Anal. Methods 6, no. 15 (2014): 5627–31. http://dx.doi.org/10.1039/c3ay41669k.

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34

Gao, Hong-Shuai, Zhi-Guo Hu, Jian-Ji Wang, Zhao-Fa Qiu, and Feng-Qiu Fan. "Synthesis and Properties of Novel Chiral Ionic Liquids from L-Proline." Australian Journal of Chemistry 61, no. 7 (2008): 521. http://dx.doi.org/10.1071/ch07298.

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A novel class of chiral ionic liquids with chiral cations directly derived from natural l-proline has been synthesized and their physical properties such as melting point, thermal degradation, and specific rotation have been characterized. Further, their potential use in chiral recognition was demonstrated by studying interactions with racemic Mosher’s acid salt.

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35

Jayachandra, R., and Sabbasani Rajasekhara Reddy. "A remarkable chiral recognition of racemic Mosher's acid salt by naturally derived chiral ionic liquids using 19F NMR spectroscopy." RSC Advances 6, no. 46 (2016): 39758–61. http://dx.doi.org/10.1039/c6ra02792j.

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36

Yu, Wei, Haibo Zhang, Long Zhang, and Xiaohai Zhou. "A Facile Strategy to Tune the Chiral Recognition Capabilities of Chiral Ionic Liquids by Changing Achiral Alkyl Chain." Australian Journal of Chemistry 63, no. 2 (2010): 299. http://dx.doi.org/10.1071/ch09333.

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A new series of chiral ionic liquids, utilizing cations derived from l-proline, have been synthesized in multi-gram scale, their specific rotations and chiral recognition capability can be adjusted by the alkylation of l-proline.

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37

Vasiloiu, Maria, Isabella Cervenka, Peter Gaertner, Matthias Weil, Christian Schröder, and Katharina Bica. "Amino alcohol-derived chiral ionic liquids: structural investigations toward chiral recognition." Tetrahedron: Asymmetry 26, no. 18-19 (October 2015): 1069–82. http://dx.doi.org/10.1016/j.tetasy.2015.08.009.

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38

Winkel, Andreas, and René Wilhelm. "New chiral ionic liquids based on imidazolinium salts." Tetrahedron: Asymmetry 20, no. 20 (October 2009): 2344–50. http://dx.doi.org/10.1016/j.tetasy.2009.09.015.

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39

Manuela A. Pereira, M. "Chiral Ionic Liquids from Carbohydrates: Synthesis and Properties." Mini-Reviews in Organic Chemistry 9, no. 3 (August 1, 2012): 243–60. http://dx.doi.org/10.2174/157019312804070426.

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40

Pereira, M. "Chiral Ionic Liquids from Carbohydrates: Synthesis and Properties." Mini-Reviews in Organic Chemistry 9, no. 3 (August 1, 2012): 243–60. http://dx.doi.org/10.2174/1570193x11209030243.

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41

Suzuki, Yumiko. "Asymmetric Michael Addition Mediated by Chiral Ionic Liquids." Mini-Reviews in Organic Chemistry 15, no. 3 (April 19, 2018): 236–45. http://dx.doi.org/10.2174/1570193x15666171211165344.

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42

Suzuki, Yumiko, Junichiro Wakatsuki, Mariko Tsubaki, and Masayuki Sato. "Imidazolium-based chiral ionic liquids: synthesis and application." Tetrahedron 69, no. 46 (November 2013): 9690–700. http://dx.doi.org/10.1016/j.tet.2013.09.017.

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43

Brown, Alexandra, Victoria Hogan, Jacob Perry, and Renuka Manchanayakage. "Chiral pool based synthesis of pyrrolidinium ionic liquids." Tetrahedron Letters 58, no. 11 (March 2017): 1061–65. http://dx.doi.org/10.1016/j.tetlet.2017.01.102.

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44

Allen, Christine R., Paulina L. Richard, Antony J. Ward, Leon G. A. van de Water, Anthony F. Masters, and Thomas Maschmeyer. "Facile synthesis of ionic liquids possessing chiral carboxylates." Tetrahedron Letters 47, no. 41 (October 2006): 7367–70. http://dx.doi.org/10.1016/j.tetlet.2006.08.007.

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45

Luo, S., J. P. Cheng, X. Mi, L. Zhang, S. Liu, and H. Xu. "Asymmetric Michael Reaction Catalyzed by Chiral Ionic Liquids." Synfacts 2006, no. 6 (June 2006): 0611. http://dx.doi.org/10.1055/s-2006-941784.

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46

Fuchs, Ido, Nina Fechler, Markus Antonietti, and Yitzhak Mastai. "Enantioselective Nanoporous Carbon Based on Chiral Ionic Liquids." Angewandte Chemie International Edition 55, no. 1 (November 11, 2015): 408–12. http://dx.doi.org/10.1002/anie.201505922.

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47

Gaumont, Annie-Claude, Yves Genisson, Frederic Guillen, Viacheslav Zgonnik, and Jean-Christophe Plaquevent. "ChemInform Abstract: Chiral Ionic Liquids for Asymmetric Reactions." ChemInform 43, no. 20 (April 23, 2012): no. http://dx.doi.org/10.1002/chin.201220256.

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48

Li, Min, Sergio L. De Rooy, David K. Bwambok, Bilal El-Zahab, John F. DiTusa, and Isiah M. Warner. "Magnetic chiral ionic liquids derived from amino acids." Chemical Communications, no. 45 (2009): 6922. http://dx.doi.org/10.1039/b917683g.

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49

Yu, Shaofang, Sergey Lindeman, and Chieu D. Tran. "Chiral Ionic Liquids: Synthesis, Properties, and Enantiomeric Recognition†." Journal of Organic Chemistry 73, no. 7 (April 2008): 2576–91. http://dx.doi.org/10.1021/jo702368t.

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50

Kapnissi-Christodoulou, Constantina P., Ioannis J. Stavrou, and Maria C. Mavroudi. "Chiral ionic liquids in chromatographic and electrophoretic separations." Journal of Chromatography A 1363 (October 2014): 2–10. http://dx.doi.org/10.1016/j.chroma.2014.05.059.

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