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Synthesis and amines enantiomeric recognition ability of binaphthyl-appended 22-crown-6 ethers derived from rosin acid

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Abstract

Novel chiral 22-crown-6 ethers (5a–b) bearing methoxycarbonyl side groups derived from rosin acid and 2,2′-dihydroxy-1,1′-binaphthyl (BINOL) were prepared in optically pure forms, and their enantiodiscriminating abilities toward protonated primary amines and amino acid methyl ester salts were examined by the UV–vis titration method. These receptors exhibit good chiral recognition towards the isomers (up to KL/KD = 5.23, ΔΔG0 = 4.10 kJ mol−1) in CHCl3:MeOH = 2:1 at 25 °C.

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Notes

  1. See in the Supplementary Data for the calculated structure of 5a and 5b by MMFF94 Minimization

References

  1. Zhang, X.X., Bradshaw, J.S., Izatt, R.M.: Enantiomeric recognition of amine compounds by chiral macrocyclic receptors. Chem. Rev. 97(8), 3313–3362 (1997). doi:10.1021/cr960144p

    Article  CAS  Google Scholar 

  2. Wenzel, T.J., Wilcox, J.D.: Chiral reagents for the determination of enantiomeric excess and absolute configuration using NMR spectroscopy. Chirality 15(3), 256–270 (2003). doi:10.1002/chir.10190

    Article  CAS  Google Scholar 

  3. Karakaplan, M., Turgut, Y.ı., Aral, T., Hoşgören, H.: The synthesis and formation of complexes between derivatives of chiral aza-18-crown-6 ethers and chiral primary organic ammonium salts. J. Incl. Phenom. Macrocycl. Chem. 54(3), 315–319 (2006)

    Article  CAS  Google Scholar 

  4. Ema, T., Tanida, D., Sakai, T.: Versatile and practical macrocyclic reagent with multiple hydrogen-bonding sites for chiral discrimination in NMR. J. Am. Chem. Soc. 129(34), 10591–10596 (2007). doi:10.1021/ja073476s

    Article  CAS  Google Scholar 

  5. Turgut, Y., Aral, T., Hosgoren, H.: Synthesis of novel C2-symmetric chiral crown ethers and investigation of their enantiomeric recognition properties. Tetrahedron Asymmetr. 20(19), 2293–2298 (2009)

    Article  CAS  Google Scholar 

  6. Lovely, A.E., Wenzel, T.J.: Chiral NMR discrimination of secondary amines using (18-crown-6)-2, 3, 11, 12-tetracarboxylic acid. Org. Lett. 8(13), 2823–2826 (2006). doi:10.1021/ol0609558

    Article  CAS  Google Scholar 

  7. Nakatsuji, Y., Nakahara, Y., Muramatsu, A., Kida, T., Akashi, M.: Novel C2-symmetric chiral 18-crown-6 derivatives with two aromatic sidearms as chiral NMR discriminating agents. Tetrahedron Lett. 46(25), 4331–4335 (2005)

    Article  CAS  Google Scholar 

  8. Turgut, Y., Demirel, N., Hoşgören, H.: Synthesis of novel chiral C 2-symmetric diaza-18-crown-6 ether derivatives and their enantioselective recognition of amino acid derivatives. J. Incl. Phenom. Macrocycl. Chem. 54(1), 29–33 (2006)

    Article  CAS  Google Scholar 

  9. Lakatos, S., Fetter, J., Bertha, F., Huszthy, P., Tóth, T., Farkas, V., Orosz, G., Hollósi, M.: Preparation of a new chiral acridino-18-crown-6 ether-based stationary phase for enantioseparation of racemic protonated primary aralkyl amines. Tetrahedron 64(6), 1012–1022 (2008)

    Article  CAS  Google Scholar 

  10. Choi, H.J., Park, Y.J., Hyun, M.H.: Liquid chromatographic resolution of secondary amino alcohols on a chiral stationary phase based on (+)-(18-crown-6)-2, 3, 11, 12-tetracarboxylic acid: Dependence of temperature effect on analyte structure. J. Chromatogr. A 1164(1–2), 235–239 (2007)

    Article  CAS  Google Scholar 

  11. Yongzhu, J., Hirose, K., Nakamura, T., Nishioka, R., Ueshige, T., Tobe, Y.: Preparation and evaluation of a chiral stationary phase covalently bound with a chiral pseudo-18-crown-6 ether having a phenolic hydroxy group for enantiomer separation of amino compounds. J. Chromatogr. A 1129(2), 201–207 (2006)

    Article  Google Scholar 

  12. Farkas, V., Tóth, T., Orosz, G., Huszthy, P., Hollósi, M.: Enantioseparation of protonated primary arylalkylamines and amino acids containing an aromatic moiety on a pyridino-crown ether based new chiral stationary phase. Tetrahedron Asymmetr. 17(12), 1883–1889 (2006)

    Article  CAS  Google Scholar 

  13. Hyun, M.H., Tan, G., Xue, J.Y.: Unusual resolution of N-(3, 5-dinitrobenzoyl)-[alpha]-amino acids on a chiral stationary phase based on (+)-(18-crown-6)-2, 3, 11, 12-tetracarboxylic acid. J. Chromatogr. A 1097(1–2), 188–191 (2005)

    Article  CAS  Google Scholar 

  14. Schlauch, M., Kos, O., Frahm, A.W.: Comparison of three chiral stationary phases with respect to their enantio- and diastereoselectivity for cyclic [beta]-substituted [alpha]-amino acids. J. Pharm. Biomed 27(3–4), 409–419 (2002)

    Article  CAS  Google Scholar 

  15. Hirose, K., Yongzhu, J., Nakamura, T., Nishioka, R., Ueshige, T., Tobe, Y.: Preparation and evaluation of a chiral stationary phase covalently bound with chiral pseudo-18-crown-6 ether having 1-phenyl-1, 2-cyclohexanediol as a chiral unit. J. Chromatogr. A 1078(1–2), 35–41 (2005)

    Article  CAS  Google Scholar 

  16. Hyun, M.H., Jin, J.S., Lee, W.: Liquid chromatographic resolution of racemic amino acids and their derivatives on a new chiral stationary phase based on crown ether. J. Chromatogr. A 822(1), 155–161 (1998). doi:10.1016/s0021-9673(98)00606-2

    Article  Google Scholar 

  17. Hirose, K., Jin, Y.Z., Nakamura, T., Nishioka, R., Ueshige, T., Tobe, Y.: Chiral stationary phase covalently bound with a chiral pseudo-18-crown-6 ether for enantiomer separation of amino compounds using a normal mobile phase. Chirality 17(3), 142–148 (2005). doi:10.1002/chir.20138

    Article  CAS  Google Scholar 

  18. Gao, M.-Z., Yang, Y.-Q., Xu, Z.-L.: Development of chiral crown ethers. Chin. J. Org. Chem. 21(7), 477–484 (2001)

    CAS  Google Scholar 

  19. Nicolas, I., Chevance, S., Maux, P.L., Simonneaux, G.: Chiral recognition of amines and amino acid derivatives by optically active ruthenium Halterman porphyrins in organic solvents and water. Tetrahedron Asymmetr. 21(13–14), 1788–1792 (2010). doi:10.1016/j.tetasy.2010.05.026

    Article  CAS  Google Scholar 

  20. Brunet, E., Poveda, A.M., Rabasco, D., Oreja, E., Font, L.M., Batra, M.S., Rodriguez-Ubis, J.C.: New chiral crown ethers derived from camphor and their application to asymmetric Michael addition. First attempts to rationalize enantioselection by AM1 and AMBER calculations. Tetrahedron Asymmetr 5(5), 935–948 (1994)

    Article  CAS  Google Scholar 

  21. Ayer, W.A., Mcdonald, C.E.: The stereochemistry of maleopimaric acid and the long range shielding effect of the olefinic bond. Can. J. Chem. 41, 1113–1126 (1963)

    Article  CAS  Google Scholar 

  22. Tolstikov, A.H., Tolstikova, O.V., Khlebnikova, T.B., Karpyshev, N.N.: Higer terpenoids in the synthesis of chiral phosphor-and nitrogen-containing ligands for metal-complex catalysts of asymmetric reactions. Chem. Comput. Simul. Butl. Commun. 2(7), 1–8 (2002)

    Google Scholar 

  23. Ye, F.G., Wang, H.S., Huang, B.J., Zhao, S.L.: Maleopimaric acid anhydride-bonded silica monolith as chiral stationary phase for separations of phenylthiocarbamyl amino acids by CEC. Electrophoresis 31(9), 1488–1492 (2010). doi:10.1002/elps.200900716

    CAS  Google Scholar 

  24. Wang, H., Zhao, S., He, M., Zhao, Z., Pan, Y., Liang, Q.: Sodium maleopimaric acid as pseudostationary phase for chiral separations of amino acid derivatives by capillary micellar electrokinetic chromatography. J. Sep. Sci. 30(16), 2748–2753 (2007)

    Article  CAS  Google Scholar 

  25. Zhao, S.L., Wang, H.S., Zhang, R.C., Tang, L.D., Liu, Y.M.: Degradingdehydroabietylisothiocyanate as a chiral derivatizing reagent for enantiomeric separations by capillary electrophoresis. Electrophoresis 27(17), 3428–3433 (2006). doi:10.1002/elps.200600008

    Article  CAS  Google Scholar 

  26. Zhao, S., Zhang, R., Wang, H., Tang, L., Pan, Y.: Capillary electrophoresis enantioselective separation of vigabatrin enantiomers by precolumn derivatization with dehydroabietylisothiocyante and UV-vis detection. J. Chromatogr. B 833(2), 186–190 (2006)

    Article  CAS  Google Scholar 

  27. Wright, K., Lohier, J.-F., Wakselman, M., Mazaleyrat, J.-P., Formaggio, F., Peggion, C., De Zotti, M., Toniolo, C.: Synthesis of enantiopure, axially chiral, C[alpha]-tetrasubstituted [alpha]-amino acids with binaphthyl-based crowned side chains and 3D-structural analysis of their peptides. Tetrahedron 64(10), 2307–2320 (2008)

    Article  CAS  Google Scholar 

  28. Benniston, A.C., Gunning, P., Peacock, R.D.: Synthesis and binding properties of hybrid cyclophane–azamacrocyclic receptors. J. Org. Chem. 70(1), 115–123 (2004). doi:10.1021/jo048621o

    Article  Google Scholar 

  29. Hess, S.C., Farah, M.I.S., Eguchib, S.Y., Imamura, P.M.: Synthetic studies with Pinus elliottiis?rosin derivatives. Oxidation of maleopimaric anhydride methyl ester and trimethyl fumaropimarate. J. Brazil. Chem. Soc. 11, 59–63 (2000)

    Article  CAS  Google Scholar 

  30. Gastambide, B., Langlois, N.: Etudes stéréochimiques VII Synthèses diéniques en série résinique; action des peroxoacides et des hydrures doubles. Helv. Chim. Acta 51, 2048–2057 (1968)

    Article  CAS  Google Scholar 

  31. Turgut, Y., Hosgören, H.: Synthesis of chiral monoaza-15-crown-5 ethers from -valinol and the enantiomeric recognition of chiral amines and their perchlorates salts. Tetrahedron Asymmetr. 14(23), 3815–3818 (2003)

    Article  CAS  Google Scholar 

  32. Hirose, K.: A practical guide for the determination of binding constants. J. Incl. Phenom. Macrocycl. Chem. 39(3), 193–209 (2001). doi:10.1023/a:1011117412693

    Article  CAS  Google Scholar 

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Acknowledgements

This study was supported by the National Natural Science Foundation of China (No. 20762001), the Project of Ten, Hundred, Thousand Distinguished Talents in New Century of Guangxi (No. 2007228), 973 project (No. 2011CB512005) and Guangxi Natural Science Foundation of China (2010GXNSFF013001; 2011GXNSFD018010).

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Authors and Affiliations

  1. Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry & Chemical Engineering of Guangxi Normal University, Guilin, 541004, People’s Republic of China

    Hengshan Wang, Chunhuan He, Yingming Pan, Guiyang Yao, Qiang Wu & Honggui Deng

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  1. Hengshan Wang
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  2. Chunhuan He
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Correspondence to Hengshan Wang.

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Wang, H., He, C., Pan, Y. et al. Synthesis and amines enantiomeric recognition ability of binaphthyl-appended 22-crown-6 ethers derived from rosin acid. J Incl Phenom Macrocycl Chem 73, 177–183 (2012). https://doi.org/10.1007/s10847-011-0040-5

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