Rozdzielenie mieszanin racemicznych za pomocą krystalizacji. Część 2, Rozdzielenie racematów z utworzeniem diastereoizomerycznych soli

• Autorzy: Kołodziejska R. , Studzińska R. , Kopkowska E. , Karczmarska-Wódzka A. , Augustyńska B.

Warianty tytułu

EN

Separation of the racemic mixtures by crystallization. Part 2, Resolution by formation of diastereomeric salts

• Języki publikacji: PL

Abstrakty

EN

The enantioseparation of a racemate through diastereomeric salt formation with a resolving agent is one of the most attractive methods for obtaining an enantiopure compound, with advantages such as its simplicity in operation, recyclability of the chiral source, and applicability on an industrial scale. In this method the enantiomers are converted into a diastereomeric salt pair by reaction with a single enantiomer of resolving agent. The diastereomers are then separated by crystallization taking advantage of the different solubility of the two compounds [1–3]. The formation of diastereomers, to be separated afterward, usually consists of salt formation with a resolving agent of opposite acide-base character (Scheme 1, 9). In this process, the molecules of opposite character (amine and acid) recognize each other by various interactions on the basis of their molecular structures and functional groups [3]. Using this method can be obtained a series of enantiomerically pure amines (Scheme 2–8) [4–26] and acids (Scheme 10–17) [27–41] which may be valuable substrates for asymmetric synthesis. The conditions for enantioseparation play an important role. On the efficiency of the enantioseparation has an effect the resolving agent, nature of the solvent or just its dielectric constant and the character and amount of some supplementary additives.

Słowa kluczowe

PL

krystalizacja; mieszanina racemiczna; rozdzielenie racemicznych amin; rozdzielenie racemicznych kwasów; diastereoizomeryczne sole

EN

crystallization; racemic mixture; resolution of racemic mixture; resolution of rac-amines; resolution of rac-acids; diastereoisomeric salts

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2015
• Tom: [Z] 69, 1-2
• Strony: 89--110
• Opis fizyczny: Bibliogr. 41 poz., schem.

Twórcy

autor

Kołodziejska R.

• Katedra i Zakład Biochemii, Collegium Medicum w Bydgoszczy, UMK Toruń ul. Karłowicza 24, 85-092 Bydgoszcz

autor

Studzińska R.

• Katedra i Zakład Chemii Organicznej, Collegium Medicum w Bydgoszczy, UMK Toruń ul. A. Jurasza 2, 85-089 Bydgoszcz

autor

Kopkowska E.

• Katedra i Zakład Biochemii, Collegium Medicum w Bydgoszczy, UMK Toruń ul. Karłowicza 24, 85-092 Bydgoszcz

autor

Karczmarska-Wódzka A.

• Katedra i Zakład Biochemii, Collegium Medicum w Bydgoszczy, UMK Toruń ul. Karłowicza 24, 85-092 Bydgoszcz

autor

Augustyńska B.

• Katedra i Zakład Biochemii, Collegium Medicum w Bydgoszczy, UMK Toruń ul. Karłowicza 24, 85-092 Bydgoszcz

Bibliografia

• [1] W.M Potapow, Stereochemia, Państwowe Wydawnictwo Naukowe, Warszawa 1986.
• [2] F. Faigl, E. Fogassy, M. Nόgradi, E. Palovics, J. Schindler, Tetrahedron: Asymmetry, 2008, 19, 519.
• [3] R. Siedlecka, Tetrahedron Asymmetry, 2013, 69, 6331.
• [4] R. Sakurai, K. Sakai, K. Kodama, M. Yamaura, Tetrahedron: Asymmetry, 2012, 23, 221.
• [5] R. Sakurai, A. Yuzawa, K. Sakai, Tetrahedron: Asymmetry, 2008, 19, 1622.
• [6] K. Sakai, R. Sakurai, M. Yokoyama, N. Hirayama, Tetrahedron: Asymmetry, 2006, 17, 1541.
• [7] T. Hirose, M. Begum, M. S. Islam, K. Taniguchi, M. Yasutake, Tetrahedron: Asymmetry, 2008, 19, 1641.
• [8] J. Schindler, M. Egressy, L. Bereczki, G. Pokol, E. Fogassy, K. Marthi, Chirality, 2007, 19, 239.
• [9] L.M. Klingensmith, K.A. Nadeau, G.A. Moniz, Tetrahedron Lett., 2007, 48, 4589.
• [10] M. Leeman, G. Brasile, E. Gelens, T. Vries, B. Kaptein, R. Kellog, Angew. Chem., Int. Ed., 2008, 47, 1287.
• [11] Y. Kobayashi, H. Handa, J. Maeda, K. Saigo, Chirality, 2008, 20, 577.
• [12] V.T. Mathad, G.B. Shinde, S.S. Ippar, N.C. Niphade, R.K. Panchangam, P.J. Vankawala, Synth. Commun., 2011, 41, 341.
• [13] K. Taniguchi, M. Aruga, M. Yasutake, T. Hirose, Org. Biomol. Chem., 2008, 6, 458.
• [14] N. Ribeiro, Y. Kobayashi, J. Maeda, K. Saigo, Chirality, 2011, 23, 438.
• [15] T. Kalai, J. Schindler, M. Balog, E. Fogassy, K. Hideg, Tetrahedron, 2008, 64, 1094.
• [16] M. Albalat-Serradeil, G. Primazot, D. Wilhelm, J.-C. Vallejos, N. Vanthuyne, C. Roussel, Amino Acids, 2012, 43, 687.
• [17] D.M. Gotrane, R.D. Deshmukh, P.V. Ranade, S.P. Sonawane, B.M. Bhawal, M.M. Gharpure, M.K. Gurjar, Org. Process Res. Dev., 2010, 14, 640.
• [18] M. Schmitt, D. Schollmeyer, S.R. Waldvogel, Eur. J. Org. Chem., 2014, 1007.
• [19] Y. Uchida, Y.Nakayama, K. Suzuki, S. Oki, M. Horiguchi, H. Tsue, R. Tamura, Heterocycles, 2008, 76, 875.
• [20] R. Ogawa, T. Fujino, N. Hirayama, K. Sakai, Tetrahedron: Asymmetry, 2008, 19, 2458.
• [21] P.S. Dragovich, D.E. Murphy, K. Dao, S.H. Kim, L.-S. Li, F. Ruebsam, Z. Sun, C.V. Tran, A.X. Xiang, Y. Zhou, Tetrahedron: Asymmetry, 2008, 19, 2796.
• [22] I. Kmecz, B. Simandi, E. Szekely, J. Lovasz, E. Fogassy, Chirality, 2007, 19, 430.
• [23] S. Shirakawa, A. Moriyama, S. Shimizu, Eur. J. Org. Chem., 2008, 5957.
• [24] J.B. III Paine, J. Org. Chem., 2008, 73, 4939.
• [25] Y.-Q. Cheng, Z. Bian, C.-Q. Kang, H.-Q. Guo, L.-X. Gao, Tetrahedron: Asymmetry, 2008, 19, 1572.
• [26] E. Gnanamani, C.R. Ramanathan, Tetrahedron: Asymmetry, 2009, 20, 2211.
• [27] P. Wang, E. Zhang, J.-F. Niu, Q.-H. Ren, P. Zhao, H.-M. Liu, Tetrahedron: Asymmetry, 2012, 23, 1046.
• [28] Q. He, Y.-F. Peng, S. Rohani, Chirality, 2010, 22, 16.
• [29] Y.-F. Peng, Q. He, S. Rohani, H. Jenkins, Chirality, 2012, 24, 349.
• [30] P. Molnar, P. Bombicz, C. Varga, L. Bereczki, E. Szekely, G. Pokol, E. Fogassy, B. Simandi, Chirality, 2009, 21, 628.
• [31] E. Palovics, J. Schindler, F. Faigl, E. Fogassy, Tetrahedron: Asymmetry, 2010, 21, 2429.
• [32] E. Palovics, L. Bereczki, K. Marthi, G. Pokol, F. Faigl, E. Fogassy, Tetrahedron: Asymmetry, 2007, 18, 2531.
• [33] M. Morimoto, A. Yamakawa, H. Katagiri, K. Sakai, Tetrahedron: Asymmetry, 2007, 18, 2869.
• [34] R. Melgar-Fernandez, R. Gonzalez-Olvera, J. Vargas-Caporali, R. Perez-Isidoro, E. Juaristi, Arkivoc, 2010, 8, 55.
• [35] Y. Uchida, T. Uematsu, Y. Nakayama, H. Takahashi, H. Tsue, K. Tanaka, R. Tamura, Chirality, 2008, 20, 282.
• [36] B. Zhang, W. He, X. Shi, M. Huan, Q. Huang, S. Zhou, Bioorg. Med. Chem. Lett., 2010, 20, 805.
• [37] Y. Kobayashi, Y. Kokubo, T. Aisaka, K. Saigo, Tetrahedron: Asymmetry, 2008, 19, 2536.
• [38] B. Kaboudin, H. Haghighat, T. Yokomatsu, Tetrahedron: Asymmetry, 2008, 19, 862.
• [39] B. Kaboudin, S. Alaie, T. Yokomatsu, Tetrahedron: Asymmetry, 2011, 22, 1813.
• [40] M. Stankevič, K.M. Pietrusiewicz, J. Org. Chem., 2007, 72, 816.
• [41] M. Stankevič, K.A. Pietrusiewicz, Tetrahedron: Asymmetry, 2007, 18, 552.