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Warianty tytułu
Tartaric acid and its derivatives in current organic chemistry
Języki publikacji
Abstrakty
The tartaric acid and its salts have been present in chemistry for almost 350 years, since Pierre Seignette isolated Rochelle salt in 1675. Since that time tartaric acid and its derivatives have been often used in chemistry due to their accessibility, enantiopurity, relatively low cost and presence of different functional groups which easily allow to modify the molecule. Many tartaric acid derivatives serve as catalysts in important stereoselective transformations such as Sharpless asymmetric epoxidation or asymmetric Rousch aryloboronation. In many others reactions tartaric acid have been employed as a chiral building block for natural products synthesis, highly functionalized molecules or ligand design such as well known TADDOL or its analogues. Its polar functional groups allow to form crystals with amines and aminoalcohols what is widely used for their enantiopurification and resolution. The relatively new subdiscipline is the use of tartaric acid in chiral recognition and chiral discrimination in nanochemistry and enantioselective chromatography. The other, recent applications of tartaric acid include functionalization of metal layers, antibacterial and antifungal activity among many others. The significance of tartaric acid is evident – since 2000, words “tartaric acid” or “tartrates” can be found in databases over four thousand times. Taking that into account this short review is concentrated on selected applications of tartaric acid and its derivatives in organic chemistry in recent several years.
Wydawca
Czasopismo
Rocznik
Tom
Strony
495--519
Opis fizyczny
Bibliogr. 73 poz., rys., schem.
Twórcy
autor
- Uniwersytet im. Adama Mickiewicza w Poznaniu, Wydział Chemii, Zakład Stereochemii Organicznej ul. Grunwaldzka 6, 60-760 Poznań
Bibliografia
- [1] L. Pasteur, Ann. Chim. Et Phys., 1848, 24, 442.
- [2] J.K. Whitesell, Chem. Rev., 1989, 89, 1581.
- [3] H.-U. Blaser, Chem. Rev., 1992, 92, 935.
- [4] D. Seebach, E. Hungerbuehler, [w:] Modern Organic Methods, R. Scheffold (ed.), Otto Salle Verlag, Frankfurt 1980.
- [5] S. Hanessian, The Total Synthesis of Natural Products: The Chiron Approach, Pergamon Press, New York 1983.
- [6] J. Gawroński, K. Gawrońska, Tartaric and Malic Acids in Synthesis, J. Wiley & Sons, New York 1999.
- [7] K. Zhang, M. Wang, D. Wang, C.J. Gao, J. Membr. Sci., 2009, 341, 246.
- [8] K. Zhang, M. Wang, C.J. Gao, J. Membr. Sci., 2011, 366, 266.
- [9] K. Zhang, M. Wang, C.J. Gao, J. Membr. Sci., 2012, 387, 48.
- [10] C.H. Huang, T.W. Xu, Y.P. Zhang, J. Membr. Sci., 2007, 288, 1.
- [11] T.W. Xu, W.H. Yang, Chem. Eng. Process., 2002, 41, 519.
- [12] F. Alvarez, R. Alvarez, J. Coca, J. Sandeaux, R. Sandeaux, C. Gavach, J. Membr. Sci., 1997, 123, 61.
- [13] Y. Kamatani, H. Okazaki, K. Imai, N. Fujita, Y. Yamazaki, K. Ogino, U.S. patent 1977, 4,028,185.
- [14] Y. Kamatani, H. Okazaki, K. Imai, N. Fujita, Y. Yamazaki, K. Ogino, B.R.D. Patent, 1987, DE 26 00 589 C 2.
- [15] M. Rosenberg, H. Mikova, L. Kristofikova, Biotechnol. Lett., 1999, 21, 491.
- [16] R. Willaert, L. De Vuyst, Appl. Microbiol. Biotechnol., 2006, 71, 155.
- [17] K. Yamada, T. Kodama, T. Obata, N. Takahasi, J. Ferment. Technol., 1972, 49, 85.
- [18] T. Kodama, U. Kotera, K. Yamada, Agric. Biol. Chem., 1972, 36, 1299.
- [19] U. Kotera, T. Kodama, Y. Minoda, K. Yamada, Agric. Biol. Chem., 1972, 36, 1315.
- [20] H.F. Bhat, G.N. Qazi, S.K. Chaturvedi, C.L. Chopra, Res. Ind., 1986, 31, 148.
- [21] D. Mantha, Z.A. Basha, T. Panda, Bioproc. Eng., 1998, 19, 285.
- [22] K. Chandrashekar, P.A. Felse, T. Panda, Bioprocess. Eng., 1999, 20, 203.
- [23] J. Gawroński, K. Gawrońska, N. Waścinska, A. Plutecka, U. Rychlewska, Pol. J. Chem., 2007, 81, 1917.
- [24] U. Rychlewska, N. Waścinska, B. Warżajtis, J. Gawroński, Acta Cryst., 2008, B64, 497.
- [25] R. Cysewski, M. Kwit, B. Warżajtis, U. Rychlewska, J. Gawroński, J. Org. Chem., 2009, 74, 4573.
- [26] H.-J. Kim, S. Sakamoto, K. Yamaguchi, J.-I. Hong, Org. Lett., 2003, 5, 1051.
- [27] J. Gawroński, J. Grajewski, Org. Lett., 2003, 5, 3301.
- [28] M. Hoffmann, J. Grajewski, J. Gawroński, New J. Chem., 2010, 34, 2020.
- [29] J. Gawroński, A. Długokińska, J. Grajewski, A. Plutecka, U. Rychlewska, Chirality, 2005, 17, 388.
- [30] M. Hoffmann, J. Rychlewski, U. Rychlewska, J. Am. Chem. Soc., 1999, 121, 1912.
- [31] L. Synoradzki, P. Ruśkowski, U. Bernaś, Org. Prep. Proced. Int., 2005, 37, 37.
- [32] A. Guarna, A. Guidi, F. Machetti, G. Menchi, E. G. Occhiato, D. Scarpi, S. Sisi, A. Trabocchi, J. Org. Chem., 1999, 64, 9865.
- [33] A. Giannis, T. Kolter, Angew. Chem. Int. Ed., 1993, 32, 1244.
- [34] F. Massicot, N. Monnier-Benoit, N. Deka, R. Plantier-Royon, C. Portella J. Org. Chem., 2007, 72, 1174.
- [35] D. Harakat, F. Massicot, J. Nonnenmacher, F. Grellepois, C. Portella Chem. Eur. J., 2011, 17, 10636.
- [36] M. Ziołkowski, Z. Czarnocki, Tetrahedron Lett., 2000, 41, 1963.
- [37] D. Mostowicz, R. Wojcik, G. Dołęga, Z. Kałuża, Tetrahedron Lett., 2004, 45, 6011.
- [38] K.F. Albizati, S. Babu, A. Birchler, J. K. Busse, M. Fugett, A. Grubbs, A. Haddach, M. Pagan, B. Potts, T. Remarchuk, D. Rieger, R. Rodriguez, J. Shanley, R. Szendroi, T. Tibbetts, K. Whitten, B.C. Borer, Tetrahedron Lett., 2001, 42, 6481.
- [39] M. Takinami, Y. Ukaji, K. Inomata, Tetrahedron: Asymmetry, 2006, 17, 1554.
- [40] M.T. Barros, A.J. Burke, J.-D. Lou, C.D. Maycock, J.R. Wahnon, J. Org. Chem., 2004, 69, 7847.
- [41] D.A. Evans, B.W. Trotter, J.C. Barrow, Tetrahedron, 1997, 53, 8779.
- [42] J.J. Bou, A. Rodriguez-Galin, S. Munoz-Guerra, Macromolecules, 1993, 26, 5664.
- [43] J.J. Bou, I. Iribarren, S. Munoz-Guerra, Macromolecules, 1994, 27, 5263.
- [44] I.A. Mathakiya, A.K. Rakshit, Int. J. Polym. Mater., 2004, 53, 405.
- [45] H. Kimura, T. Yoshinari, M. Takeishi, Polym. J. 1999, 31, 338.
- [46] I. Villuendas, J.I. Iribarren, S. Munoz-Guerra, Macromolecules, 1999, 32, 8015.
- [47] A. Alia, A. Rodriguez-Galfin, A. Martinez de Ilarduya, S. Munoz-Guerra, Polymer, 1997, 38, 4935.
- [48] M. Acemoglu, S. Bantle, T. Mindt, F. Nimmerfall, Macromolecules, 1995, 28, 3030.
- [49] M. Yokoe, K. Aoi, M. Okada, J. Polym.Sci., Part A: Polym. Chem., 2005, 43, 3909.
- [50] B. Li, X. Yang, K. Yang, E. Fu Synth. Commun., 2005, 35, 2603.
- [51] R. Wu, T.F. Al-Azemi, K.S. Bisht, Biomacromolecules, 2008, 9, 2921.
- [52] J.J. Bou, I. Iribarren, A. Martınez De Ilarduya, S. Munoz-Guerra, J. Polym. Sci.: Part A: Polym. Chem., 1999, 37, 983.
- [53] M.A. Majo, A. Alla, J.J. Bou, C. Herranz, S. Munoz-Guerra, Eur. Polym. J., 2004, 40, 2699.
- [54] D. Seebach, A.K. Beck, A. Heckel, Angew. Chem. Int. Ed., 2001, 40, 92.
- [55] R.A. Johnson, K. B. Sharpless, Comp. Org. Syn., 1991, 7, 389.
- [56] E. Huft, Top. Curr. Chem., 1993, 164, 63.
- [57] T. Katsuki, V. S. Martin, Org. React., 1996, 48, 1.
- [58] S. Nakagawa, A. Tai, T. Okuyama, T. Sugimura, Top. Catal., 2000, 13 187.
- [59] T. Sugimura, T. Matsuda, T. Osawa, Tetrahedron: Asymmetry 2009, 20, 1877.
- [60] A. Hui, J. Zhang, J. Fan, Z. Wang, Tetrahedron: Asymmetry, 2006, 17, 2101.
- [61] H. Ube, S. Fukuchi, M. Terada, Tetrahedron: Asymmetry, 2010, 21, 1203.
- [62] C. Gan, Can. J. Chem., 2008, 86, 261.
- [63] S. Arai, R. Tsuji, A. Nishida, Tetrahedron Lett., 2002, 43, 9535.
- [64] S. Murakami, S. Habaue, H. Higashimura, Polymer, 2007, 48, 6565.
- [65] L. Synoradzki, U. Bernaś, P. Ruśkowski, Org. Prep. Proced. Int., 2008, 40, 163.
- [66] K. Takabe, M. Sugiura, Y. Asumi, N. Mase, H. Yoda, H. Shimizu, Tetrahedron Lett., 2005, 46, 3457.
- [67] K. Tanaka, S. Honke, Z. Urbanczyk-Lipkowska, F. Toda, Eur. J. Org. Chem., 2000, 3171.
- [68] J. Oxelbark, P. Gidlund, Chirality, 2005, 17, 79.
- [69] O. Gyllenhaal, A. Karlsson, J. Biochem. Biophys. Methods, 2002, 54, 169.
- [70] W. Weng, Q.H. Wang, B.X. Yao, Q. Le Zeng, J. Chromatog. A, 2004, 1042, 81.
- [71] B. Tan, G.-S. Luo, X. Qi, J. Wang, Sep. Purif. Technol., 2006, 49, 186.
- [72] Y. Ferrand, A.M. Kendhale, B. Kauffmann, A. Grelard, C. Marie, V. Blot, M. Pipelier, D. Dubreuil, I. Huc, J. Am. Chem. Soc., 2010, 132, 7858.
- [73] B. Li, X. Yang, X. Wu, Z. Luo, C. Zhong, E. Fu, Supramol. Chem., 2006, 18, 507.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-c1528888-019b-42f9-a614-b4d798be24b9