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Journal articles on the topic 'Chiral solvating agents'

Author: Grafiati
Published: 6 September 2023

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1

Giordano, Claudio, and Angelo Restelli. "New chiral solvating agents: 1,5-Benzothiazepines." Tetrahedron: Asymmetry 2, no. 8 (January 1991): 785–88. http://dx.doi.org/10.1016/s0957-4166(00)80460-7.

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2

Li, Gao-Wei, Xiao-Juan Wang, Dan-Dan Cui, Yu-Fei Zhang, Rong-Yao Xu, Shuai-Hua Shi, Lan-Tao Liu, Min-Can Wang, Hong-Min Liu, and Xin-Xiang Lei. "Azaheterocyclic diphenylmethanol chiral solvating agents for the NMR chiral discrimination of alpha-substituted carboxylic acids." RSC Advances 10, no. 57 (2020): 34605–11. http://dx.doi.org/10.1039/d0ra06312f.

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Chiral azaheterocycle-containing diphenylmethanols with multiple hydrogen-bonding sites were described and used as NMR chiral solvating agents (CSAs). Highly resolved NMR spectra can be obtained directly in the NMR tube.
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3

Fang, Lixia, Caixia Lv, Guo Wang, Lei Feng, Pericles Stavropoulos, Guangpeng Gao, Lin Ai, and Jiaxin Zhang. "Discrimination of enantiomers of dipeptide derivatives with two chiral centers by tetraaza macrocyclic chiral solvating agents using 1H NMR spectroscopy." Organic Chemistry Frontiers 3, no. 12 (2016): 1716–24. http://dx.doi.org/10.1039/c6qo00521g.

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4

Zhang, Hanchang, Hongmei Zhao, Jie Wen, Zhanbin Zhang, Pericles Stavropoulos, Yanlin Li, Lin Ai, and Jiaxin Zhang. "Discrimination of enantiomers of amides with two stereogenic centers enabled by chiral bisthiourea derivatives using 1H NMR spectroscopy." Organic & Biomolecular Chemistry 19, no. 30 (2021): 6697–706. http://dx.doi.org/10.1039/d1ob00742d.

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5

Gunaratne, H. Q. Nimal, Tiina Laaksonen, Kenneth R. Seddon, and Kristiina Wähälä. "1-(+)-Dehydroabietylimidazolium Salts as Enantiomer Discriminators for NMR Spectroscopy." Australian Journal of Chemistry 70, no. 7 (2017): 845. http://dx.doi.org/10.1071/ch16545.

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Nine new (+)-dehydroabietylimidazolium salts were synthesised and studied as chiral solvating agents for several different racemic aromatic and non-aromatic carboxylate salts. These cationic chiral solvating agents resolve racemic ionic analytes better than non-ionic ones. Bis(dehydroabietylimidazolium) bis(trifluoromethanesulfonimide) gave the best discrimination for the enantiomers of carboxylate salts. Its resolution behaviour was studied by an NMR titration experiment, which indicated 1 : 1 complexation with the racemic analyte. The dehydroabietylimidazolium salts were also useful in enantiomeric excess (ee) determinations, and for the recognition of chirality of racemic aromatic and non-aromatic α-substituted carboxylic acids.
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6

Li, Gaowei, Jiangming Cao, Wen Zong, Xinxiang Lei, and Renxiang Tan. "Enantiodiscrimination of carboxylic acids using the diphenylprolinol NMR chiral solvating agents." Organic Chemistry Frontiers 3, no. 1 (2016): 96–102. http://dx.doi.org/10.1039/c5qo00264h.

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7

Moon, Lomary S., Mohan Pal, Yoganjaneyulu Kasetti, Prasad V. Bharatam, and Ravinder S. Jolly. "Chiral Solvating Agents for Cyanohydrins and Carboxylic Acids†." Journal of Organic Chemistry 75, no. 16 (August 20, 2010): 5487–98. http://dx.doi.org/10.1021/jo100445d.

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8

Uccello-Barretta, Gloria, Federica Balzano, Jonathan Martinelli, Margherita-Giulia Berni, Claudio Villani, and Francesco Gasparrini. "NMR enantiodiscrimination by cyclic tetraamidic chiral solvating agents." Tetrahedron: Asymmetry 16, no. 22 (November 2005): 3746–51. http://dx.doi.org/10.1016/j.tetasy.2005.10.016.

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9

GIORDANO, C., and A. RESTELLI. "ChemInform Abstract: New Chiral Solvating Agents: 1,5-Benzothiazepines." ChemInform 22, no. 47 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199147290.

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10

Lv, Caixia, Lei Feng, Hongmei Zhao, Guo Wang, Pericles Stavropoulos, and Lin Ai. "Chiral discrimination of α-hydroxy acids and N-Ts-α-amino acids induced by tetraaza macrocyclic chiral solvating agents by using 1H NMR spectroscopy." Organic & Biomolecular Chemistry 15, no. 7 (2017): 1642–50. http://dx.doi.org/10.1039/c6ob02578a.

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11

Tayama, Eiji, and Takeshi Sugawara. "Chiral Tetraaryl- and Tetraalkynylborates as Chiral Solvating Agents for Tetraalkylammonium Salts." European Journal of Organic Chemistry 2019, no. 4 (January 11, 2019): 803–11. http://dx.doi.org/10.1002/ejoc.201801448.

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12

Chaudhary, Pooja, Geeta Devi Yadav, and Surendra Singh. "A simple protocol for determination of enantiopurity of amines using BINOL derivatives as chiral solvating agents via1H- and 19F-NMR spectroscopic analysis." RSC Advances 12, no. 39 (2022): 25457–64. http://dx.doi.org/10.1039/d2ra05291a.

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A rapid and simple protocol for the determination of enantiopurity of primary and secondary amines was developed by using enantiopure BINOL and their derivatives as chiral solvating agents via1H- and 19F-NMR spectroscopic analysis.
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13

Liu, Luzhi, Cuiguang Ma, Qin He, Yan Huang, and Wengui Duan. "Effective enantiomeric identification of aromatic amines by tyrosine-modified pillar[5]arenes as chiral NMR solvating agents." Organic Chemistry Frontiers 8, no. 15 (2021): 4144–52. http://dx.doi.org/10.1039/d1qo00525a.

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Two novel tyrosine-modified pillar[5]arenes have been synthesized and applied as chiral NMR solvating agents to establish an efficient 1H NMR method for enantioselective recognition and configuration assignment towards α-aromatic ethylamines.
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14

Merelli, Bérangère, Laurence Menguy, Estelle Soubeyrand-Lenoir, and Jean-Claude Cherton. "Determination of the enantiomeric composition of chiral delta-2-thiazolines-1,3 by1H and19F NMR spectroscopy using chiral solvating agents." Spectroscopy 20, no. 3 (2006): 95–107. http://dx.doi.org/10.1155/2006/698685.

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Studies of the perturbing effect of chiral solvating agents (CSAs) namely the fluoroalcohols5aand5bupon the NMR spectra of chiral Δ2-thiazolines1presenting interesting insecticidal properties demonstrated the ability of these CSAs to afford diastereomeric solvates from these substrates providing their enantiomeric discrimination. Thus, for five of the six tested Δ2-thiazolines1Aand1Bthere is at least one possibility to proceed to their enantiomeric discrimination either by1H or19F NMR using mostly5bas CSA.
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15

Yuan, Quan, Enqin Fu, Xiaojun Wu, Maohai Fang, Peng Xue, Chengtai Wu, and Jiahua Chen. "A convenient synthesis of chiral dioxocyclens and application as chiral solvating agents." Tetrahedron Letters 43, no. 21 (May 2002): 3935–37. http://dx.doi.org/10.1016/s0040-4039(02)00623-8.

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16

Periasamy, Mariappan, Manasi Dalai, and Meduri Padmaja. "Chiral trans-1,2-diaminocyclohexane derivatives as chiral solvating agents for carboxylic acids." Journal of Chemical Sciences 122, no. 4 (July 2010): 561–69. http://dx.doi.org/10.1007/s12039-010-0090-z.

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17

Laaksonen, Tiina, Sami Heikkinen, and Kristiina Wähälä. "Synthesis and applications of secondary amine derivatives of (+)-dehydroabietylamine in chiral molecular recognition." Organic & Biomolecular Chemistry 13, no. 42 (2015): 10548–55. http://dx.doi.org/10.1039/c5ob01667c.

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(+)-Dehydroabietylamine (1a), the novel derivatives (2a–6a) and their NTf2 salts (1b–6b) were tested as chiral NMR solvating agents for the resolution of enantiomers of Mosher's acid and other carboxylic acids, and their n-Bu4N salts.
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18

Labuta, Jan, Shinsuke Ishihara, Daniel T. Payne, Kazuyoshi Takimoto, Hisako Sato, Lenka Hanyková, Katsuhiko Ariga, and Jonathan P. Hill. "Estimation of Enantiomeric Excess Based on Rapid Host–Guest Exchange." Chemosensors 9, no. 9 (September 9, 2021): 259. http://dx.doi.org/10.3390/chemosensors9090259.

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Chiral molecules possess enantiomers that have non-superimposable chemical structures but exhibit identical nuclear magnetic resonance (NMR) spectra. This feature prevents the use of NMR spectroscopic methods for the determination of enantiomeric excesses (ee) of chiral molecules, using simple mixtures of their enantiomers. Recently, however, it was reported that the addition of a symmetrical prochiral molecule (a reporter or host) into a solution of chiral analyte can lead to estimation of ee through interactions involving rapid exchange of the chiral analyte (guest) in the formed host–guest complex. This is due to the ee-dependent splitting of NMR resonances of the prochiral host molecule based on averaging the chemical shift non-equivalency caused by the presence of a chiral guest. The mechanism is not dependent on diastereomer formation, and 1:1 host–guest complexes can also show ee-dependent NMR peak splitting. Prochiral molecules capable of ee sensing using the NMR technique are now referred to as so-called prochiral solvating agents (pro-CSAs). pro-CSAs represent a family of reagents distinct from the commonly used NMR chiral derivatizing reagents (where chiral auxiliaries are used to derivatize enantiomers to diastereomers) or chiral solvating agents (where chiral auxiliaries interact in an asymmetric manner with analyte enantiomers). pro-CSA methods are unique since neither pro-CSA nor NMR contains chiral factors, making the technique neutral with respect to chirality. Here, we review our recent work on this matter involving several different nominally achiral receptor molecules whose unique guest binding properties and solution characteristics (especially with regard to NMR spectroscopy) allow for the estimation of ee in the corresponding chiral guests.
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19

Luu, Quang H., Kyle G. Lewis, Anik Banerjee, Nattamai Bhuvanesh, and John A. Gladysz. "The robust, readily available cobalt(iii) trication [Co(NH2CHPhCHPhNH2)3]3+ is a progenitor of broadly applicable chirality and prochirality sensing agents." Chemical Science 9, no. 22 (2018): 5087–99. http://dx.doi.org/10.1039/c8sc01510d.

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Salts of the title trication are the best chiral solvating agents found to date in terms of applicability to a broad spectrum of analytes, use at low loadings (avg 34 and 14 mol%, 2X−BAr4− salts (X = Cl, I), and ability to analyze mixtures.
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20

Bozkurt, Selahattin. "Calixarene based chiral solvating agents for α-hydroxy carboxylic acids." Journal of Molecular Structure 1048 (September 2013): 113–20. http://dx.doi.org/10.1016/j.molstruc.2013.05.032.

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21

Wenzel, Thomas J. "Calixarenes and calix[4]resorcinarenes as chiral NMR solvating agents." Journal of Inclusion Phenomena and Macrocyclic Chemistry 78, no. 1-4 (April 30, 2013): 1–14. http://dx.doi.org/10.1007/s10847-013-0325-y.

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22

Rudzińska-Szostak, Ewa, Łukasz Górecki, Łukasz Berlicki, Katarzyna Ślepokura, and Artur Mucha. "Zwitterionic Phosphorylated Quinines as Chiral Solvating Agents for NMR Spectroscopy." Chirality 27, no. 10 (August 25, 2015): 752–60. http://dx.doi.org/10.1002/chir.22494.

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23

Puentes, Cira Mollings, and Thomas J. Wenzel. "Phosphated cyclodextrins as water-soluble chiral NMR solvating agents for cationic compounds." Beilstein Journal of Organic Chemistry 13 (January 6, 2017): 43–53. http://dx.doi.org/10.3762/bjoc.13.6.

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The utility of phosphated α-, β- and γ-cyclodextrins as water-soluble chiral NMR solvating agents for cationic substrates is described. Two sets of phosphated cyclodextrins, one with degrees of substitution in the 2–6 range, the other with degrees of substitution in the 6–10 range, are examined. Results with 33 water-soluble cationic substrates are reported. We also explored the possibility that the addition of paramagnetic lanthanide ions such as praseodymium(III) and ytterbium(III) further enhances the enantiomeric differentiation in the NMR spectra. The chiral differentiation with the phosphated cyclodextrins is compared to prior results obtained with anionic carboxymethylated cyclodextrins. There are a number of examples where a larger differentiation is observed with the phosphated cyclodextrins.
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24

Luo, Zengwei, Baohua Li, Xiantao Fang, Kai Hu, Xiaojun Wu, and Enqin Fu. "Novel chiral solvating agents derived from natural amino acid: enantiodiscrimination for chiral α-arylalkylamines." Tetrahedron Letters 48, no. 10 (March 2007): 1753–56. http://dx.doi.org/10.1016/j.tetlet.2007.01.036.

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25

PERIASAMY, MARIAPPAN, MANASI DALAI, and MEDURI PADMAJA. "Erratum to: Chiral trans-1,2-diaminocyclohexane derivatives as chiral solvating agents for carboxylic acids." Journal of Chemical Sciences 123, no. 3 (May 2011): 365. http://dx.doi.org/10.1007/s12039-011-0144-x.

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26

Sheshenev, Andrey E., Ekaterina V. Boltukhina, Anastasiya A. Grishina, Ivana Cisařova, Ilya M. Lyapkalo, and King Kuok Mimi Hii. "New Chiral Zwitterionic Phosphorus Heterocycles: Synthesis, Structure, Properties and Application as Chiral Solvating Agents." Chemistry - A European Journal 19, no. 25 (April 18, 2013): 8136–43. http://dx.doi.org/10.1002/chem.201300062.

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27

Błaszczyk, Jarosław, Bogdan Bujnicki, Patrycja Pokora-Sobczak, Grażyna Mielniczak, Lesław Sieroń, Piotr Kiełbasiński, and Józef Drabowicz. "New Optically Active tert-Butylarylthiophosphinic Acids and Their Selenium Analogues as the Potential Synthons of Supramolecular Organometallic Complexes: Syntheses and Crystallographic Structure Determination." Molecules 28, no. 11 (May 24, 2023): 4298. http://dx.doi.org/10.3390/molecules28114298.

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The aim of the research described in this publication is two-fold. The first is a detailed description of the synthesis of a series of compounds containing a stereogenic heteroatom, namely the optically active P-stereogenic derivatives of tert-butylarylphoshinic acids bearing sulfur or selenium. The second is a detailed discussion dedicated to the determination of their structures by an X-ray analysis. Such a determination is needed when considering optically active hetero-oxophosphoric acids as new chiral solvating agents, precursors of new chiral ionic liquids, or ligands in complexes serving as novel organometallic catalysts.
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28

Quinn, Thomas P., Philip D. Atwood, Joseph M. Tanski, Tyler F. Moore, and J. Frantz Folmer-Andersen. "Aza-Crown Macrocycles as Chiral Solvating Agents for Mandelic Acid Derivatives." Journal of Organic Chemistry 76, no. 24 (December 16, 2011): 10020–30. http://dx.doi.org/10.1021/jo2018203.

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29

Benedict, Brooke, Christopher E. Lietz, and Thomas J. Wenzel. "Comparison of chiral NMR solvating agents for the enantiodifferentiation of amines." Tetrahedron 74, no. 37 (September 2018): 4846–56. http://dx.doi.org/10.1016/j.tet.2018.07.053.

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30

Yang, Lu, Thomas Wenzel, R. Thomas Williamson, Melodie Christensen, Wes Schafer, and Christopher J. Welch. "Expedited Selection of NMR Chiral Solvating Agents for Determination of Enantiopurity." ACS Central Science 2, no. 5 (April 20, 2016): 332–40. http://dx.doi.org/10.1021/acscentsci.6b00062.

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31

Liu, Lu, Mingde Ye, Xingen Hu, Xiaochun Yu, Lixue Zhang, and Xinxiang Lei. "Chiral solvating agents for carboxylic acids based on the salen moiety." Tetrahedron: Asymmetry 22, no. 16-17 (September 2011): 1667–71. http://dx.doi.org/10.1016/j.tetasy.2011.09.022.

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32

Zonta, Cristiano, Andrej Kolarovic, Miriam Mba, Marta Pontini, E. Peter KÜndig, and Giulia Licini. "Enantiopure Ti(IV) amino triphenolate complexes as NMR chiral solvating agents." Chirality 23, no. 9 (August 17, 2011): 796–800. http://dx.doi.org/10.1002/chir.20994.

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33

Wang, Wenge, Fengnian Ma, Xiumin Shen, and Cong Zhang. "New chiral auxiliaries derived from (S)-α-phenylethylamine as chiral solvating agents for carboxylic acids." Tetrahedron: Asymmetry 18, no. 7 (April 2007): 832–37. http://dx.doi.org/10.1016/j.tetasy.2007.03.030.

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34

Wang, Wenge, Xiumin Shen, Fengnian Ma, Zijing Li, and Cong Zhang. "Chiral amino alcohols derived from natural amino acids as chiral solvating agents for carboxylic acids." Tetrahedron: Asymmetry 19, no. 10 (May 2008): 1193–99. http://dx.doi.org/10.1016/j.tetasy.2008.04.030.

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35

Feng, Si, Liangyuan Yao, Fengliang Liu, Xiao Zeng, and Junjie Wang. "Synthesis of noval chiral tridentate amino alcohols as chiral solvating agents under ball-milling conditions." Tetrahedron Letters 59, no. 49 (December 2018): 4305–10. http://dx.doi.org/10.1016/j.tetlet.2018.10.049.

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36

Koy, Cornelia, Manfred Michalik, Christian Döbler, and Günther Oehme. "Chiral Recognition of Aminoalcohols by1H and13C NMR Spectroscopy using binaphthyl derivatives as chiral solvating agents." Journal für Praktische Chemie/Chemiker-Zeitung 339, no. 1 (1997): 660–63. http://dx.doi.org/10.1002/prac.199733901119.

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37

Erol Gunal, Sule, Senel Teke Tuncel, and Ilknur Dogan. "Enantiodiscrimination of carboxylic acids using single enantiomer thioureas as chiral solvating agents." Tetrahedron 76, no. 18 (May 2020): 131141. http://dx.doi.org/10.1016/j.tet.2020.131141.

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38

Pérez-Trujillo, Míriam, Eva Monteagudo, and Teodor Parella. "13C NMR Spectroscopy for the Differentiation of Enantiomers Using Chiral Solvating Agents." Analytical Chemistry 85, no. 22 (November 6, 2013): 10887–94. http://dx.doi.org/10.1021/ac402580j.

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39

Ma, Fengnian, Xiumin Shen, Jie Ou-Yang, Zhiwei Deng, and Cong Zhang. "Macrocyclic compounds as chiral solvating agents for phosphinic, phosphonic, and phosphoric acids." Tetrahedron: Asymmetry 19, no. 1 (January 2008): 31–37. http://dx.doi.org/10.1016/j.tetasy.2007.12.004.

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40

Dalvano, Brielle E., and Thomas J. Wenzel. "Sulfated cyclodextrins as water-soluble chiral NMR solvating agents for cationic compounds." Tetrahedron: Asymmetry 28, no. 8 (August 2017): 1061–69. http://dx.doi.org/10.1016/j.tetasy.2017.07.003.

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41

Wenzel, Thomas J. "ChemInform Abstract: Calixarenes and Calix[4]resorcinarenes as Chiral NMR Solvating Agents." ChemInform 46, no. 11 (February 24, 2015): no. http://dx.doi.org/10.1002/chin.201511347.

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42

Hoffmann, Herbert C., Silvia Paasch, Philipp Müller, Irena Senkovska, Mohan Padmanaban, Frank Glorius, Stefan Kaskel, and Eike Brunner. "Chiral recognition in metal–organic frameworks studied by solid-state NMR spectroscopy using chiral solvating agents." Chemical Communications 48, no. 85 (2012): 10484. http://dx.doi.org/10.1039/c2cc35366k.

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43

Yang, Xuemei, Xiaojun Wu, Maohai Fang, Quan Yuan, and Enqin Fu. "Novel rigid chiral macrocyclic dioxopolyamines derived from l-proline as chiral solvating agents for carboxylic acids." Tetrahedron: Asymmetry 15, no. 16 (August 2004): 2491–97. http://dx.doi.org/10.1016/j.tetasy.2004.07.016.

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44

Yi, Jingyu, Guoxin Du, Yaxi Yang, Yuanchao Li, Yiming Li, and Fujiang Guo. "Chiral discrimination of natural isoflavanones using (R)- and (S)-BINOL as the NMR chiral solvating agents." Tetrahedron: Asymmetry 27, no. 22-23 (December 2016): 1153–59. http://dx.doi.org/10.1016/j.tetasy.2016.09.002.

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45

Tabassum, Sobia, Mazhar Amjad Gilani, and René Wilhelm. "Imidazolinium sulfonate and sulfamate zwitterions as chiral solvating agents for enantiomeric excess calculations." Tetrahedron: Asymmetry 22, no. 16-17 (September 2011): 1632–39. http://dx.doi.org/10.1016/j.tetasy.2011.09.018.

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46

O'Farrell, Courtney M., J. Matthew Chudomel, Jan M. Collins, Catherine F. Dignam, and Thomas J. Wenzel. "Water-Soluble Calix[4]resorcinarenes with Hydroxyproline Groups as Chiral NMR Solvating Agents." Journal of Organic Chemistry 73, no. 7 (April 2008): 2843–51. http://dx.doi.org/10.1021/jo702751z.

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47

Wilhelm, René, Mazhar Gilani, and Eduard Rais. "Chiral Imidazolinium Salts with TIPS Groups for the Palladium-Catalyzed α-Arylation and as Chiral Solvating Agents." Synlett 26, no. 11 (June 18, 2015): 1638–41. http://dx.doi.org/10.1055/s-0034-1381012.

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48

Yang, Xuemei, Guitao Wang, Cheng Zhong, Xiaojun Wu, and Enqin Fu. "Novel NMR chiral solvating agents derived from (1R,2R)-diaminocyclohexane: synthesis and enantiodiscrimination for chiral carboxylic acids." Tetrahedron: Asymmetry 17, no. 6 (March 2006): 916–21. http://dx.doi.org/10.1016/j.tetasy.2006.03.011.

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49

Altava, Belén, M. Isabel Burguete, Noèlia Carbó, Jorge Escorihuela, and Santiago V. Luis. "Chiral bis(amino amides) as chiral solvating agents for enantiomeric excess determination of α-hydroxy and arylpropionic acids." Tetrahedron: Asymmetry 21, no. 8 (April 2010): 982–89. http://dx.doi.org/10.1016/j.tetasy.2010.05.010.

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50

O’Farrell, Courtney M., and Thomas J. Wenzel. "Water-soluble calix[4]resorcinarenes as chiral NMR solvating agents for phenyl-containing compounds." Tetrahedron: Asymmetry 19, no. 15 (August 2008): 1790–96. http://dx.doi.org/10.1016/j.tetasy.2008.07.023.

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