An aspect of selecting resolving agents: The role of differences in molecule length in diastereomeric salt resolutions

References

• Pasteur, L. (1853) Transformation des acides tartriques en acide. Découverte de l’acide tartrique inactif. Nouvelle méthode de séparation de l’acide racémique en acides tartriques droit et gauche. C. R. Acad. Sci., 26: 162.
   Google Scholar
• Jacques, J. C.; Collet, A.; Willen, S. H. (1981) Enantiomers, Racemates, and Resolutions; John Wiley: New York.
   Google Scholar
• Eliel, E. L.; Wilen, S. H.; Mander, L. N. (1994) Stereochemistry of Organic Compounds; Wiley-Interscience: New York.
   Google Scholar
• Kozma, D. (2002) CRC Handbook of Optical Resolutions via Diastereomeric Salt Formation, CRC Press: London.
   Google Scholar
• Faigl, F.; Fogassy, E.; Nógrádi, M.; Pálovics, E.; Schindler, J. (2008) Strategies in optical resolution: A practical guide. Tetrahedron: Asymmetry, 19 (5): 519.
   Web of Science ®Google Scholar
• Siedlecka, R. (2013) Recent developments in optical resolution. Tetrahedron, 69 (31): 6331.
   Web of Science ®Google Scholar
• Newman, P. (1978-1984) Optical Resolution Procedures for Chiral Compounds 1-3; Optical Resolutions Information Center: New York.
   Google Scholar
• Lorenz, H.; Seidel-Morgenstern, A. (2014) Processes to separate enantiomers. Angew. Chem. Int. Ed., 53 (5): 1218.
   PubMed Web of Science ®Google Scholar
• Pálovics, E.; Faigl, F.; Fogassy, E. (2012) Separation of the mixtures of chiral compounds by crystallization, In Advances in Crystallization Process; Mastai, Y., Ed. Intech.
   Google Scholar
• Pálovics, E.; Schindler, J.; Faigl, F.; Fogassy, E. (2012) 8.6 Physical separations: Behavior of structurally similar molecules in the resolution processes, In Comprehensive Chirality; Carreira, E. M.; Yamamoto, H., Eds.; Elsevier: Amsterdam.
   Google Scholar
• Pálovics, E.; Schindler, J.; Faigl, F.; Fogassy, E. (2010) The influence of molecular structure and crystallization time on the efficiency of diastereoisomeric salt forming resolutions. Tetrahedron: Asymmetry, 21 (19): 2429.
   Web of Science ®Google Scholar
• Pálovics, E. Structurally related compounds with common skeleton in the resolution processes. Ph.D. Dissertation, Budapest University of Technology and Economics, Budapest, 2008.
   Google Scholar
• Kozma, D.; Pokol, G.; Ács, M. (1992) Calculation of the efficiency of optical resolutions on the basis of the binary phase diagram for the diastereoisomeric salts. J. Chem. Soc., Perkin Trans. 2 (3): 435.
   Google Scholar
• Dyer, U. C.; Henderson, D. A.; Mitchell, M. B. (1999) Application of automation and thermal analysis to resolving agent selection. Org. Proc. Res. Dev., 3 (3): 161.
   Web of Science ®Google Scholar
• Borghese, A.; Libert, V.; Zhang, T.; Alt, C. A. (2004) Efficient fast screening methodology for optical resolution agents: Solvent effects are used to affect the efficiency of the resolution process. Org. Proc. Res. Dev., 8 (3): 532.
   Web of Science ®Google Scholar
• Vries, T.; Wynberg, H.; van Echten, E.; Koek, J.; ten Hoeve, W.; Kellogg, R. M.; Broxterman, Q. B.; Minnaard, A.; Kaptein, B.; van der Sluis, S.; Hulshof, L.; Kooistra, J. (1998) The family approach to the resolution of racemates. Angew. Chem. Int. Ed., 37 (17): 2349.
   Web of Science ®Google Scholar
• Nieuwenhuijzen, J. W.; Grimbergen, R. F. P.; Koopman, C.; Kellogg, R. M.; Vries, T. R.; Pouwer, K.; van Echten, E.; Kaptein, B.; Hulshof, L. A.; Broxterman, Q. B. (2002) The role of nucleation inhibition in optical resolutions with families of resolving agents. Angew. Chem. Int. Ed., 41(22): 4281.
   PubMed Web of Science ®Google Scholar
• Kellogg, R. M.; Nieuwenhuijzen, J. W.; Pouwer, K.; Vries, T. R.; Broxterman, Q. B.; Grimbergen, R. F. P.; Kaptein, B.; Crois, R. M. L.; de Wever, E.; Zwaagstra, K.; van der Laan, A. C. (2003) Dutch resolution: Separation of enantiomers with families of resolving agents. A status report. Synthesis, 10: 1626.
   Google Scholar
• Dalmolen, J.; Tiemersma-Wegman, T. D.; Nieuwenhuijzen, J. W.; van der Sluis, M.; van Echten, E.; Vries, T. R.; Kaptein, B.; Broxterman, Q. B.; Kellogg, R. M. (2005) The Dutch resolution variant of the classical resolution of racemates by formation of Diastereomeric salts: Family behavior in nucleation inhibition. Chem. - Eur. J., 11 (19): 5619.
   PubMed Web of Science ®Google Scholar
• Kinbara, K. (2005) Design of resolving agents based on crystal engineering. Synlett, 5: 732.
   Web of Science ®Google Scholar
• Saigo, K.; Kobayashi, Y. (2007) The role of CH/π interaction in the stabilization of less-soluble diastereomeric salt crystals. Chem. Rec., 7 (1): 47.
   PubMed Web of Science ®Google Scholar
• Karamertzanis, P. G.; Anandamanoharan, P. R.; Fernandes, P.; Cains, P. W.; Vickers, M.; Tocher, D. A.; Florence, A. J.; Price, S. L. (2007) Toward the computational design of diastereomeric resolving agents: An experimental and computational study of 1-phenylethylammonium-2-phenylacetate derivatives. J. Phys. Chem. B, 111 (19): 5326.
   PubMed Web of Science ®Google Scholar
• Pálovics, E.; Szeleczky, Z.; Fődi, B.; Faigl, F.; Fogassy, E. (2014) Prediction of the efficiency of diastereoisomer separation on the basis of the behavior of enantiomeric mixtures. RSC Advances, 4: 21254.
   Web of Science ®Google Scholar
• Szeleczky, Z.; Bagi, P.; Pálovics, E.; Fogassy, E. (2014) The effect of SDE on the separation of diastereomeric salts: a case study for the resolution of mandelic acid derivatives with Pregabalin. Tetrahedron: Asymmetry, 25 (15): 1095.
   Web of Science ®Google Scholar
• Szeleczky, Z.; Bagi, P.; Pálovics, E.; Fogassy, E. (2015) The effect of the eutectic composition on the outcome of kinetically and thermodynamically controlled resolutions that are based on the formation of diastereomers. Tetrahedron: Asymmetry, 26 (7): 377.
   Web of Science ®Google Scholar
• Sakai, K.; Sakurai, R.; Nohira, H. (2007) New resolution technologies controlled by chiral discrimination mechanisms, In Novel Optical Resolution Technologies, Sakai, K.; Hirayama, N.; Tamura, R., Eds.; Springer: Berlin.
   Google Scholar
• Kozma, D.; Fogassy, E. (1997) Preparative methods for enantiomeric enrichment of non-racemic enantiomeric mixtures. Enantiomer, 2 (1): 51–59.
   Google Scholar
• Fogassy, E.; Ács, M.; Felméri, J.; Aracs, J. (1976) Preparation of L-(-)-6-phenyl-2,3,5,6-tetrahydro-imidazo-(2,1-b)-thiazole. Per. Pol. Chem. Eng., 20: 248.
   Google Scholar
• Fogassy, E.; Ács, M.; Gizur, T.; Harsányi, K.; Aracs, J.; Berki, K.; Tőke, L.; Jászay, Z. Process for the resolution of threo-3-[(2-aminophenyl)thio]-2-hydroxy-3-(4-methoxyphenyl)propionic acid. WO Patent 9100270, Jun. 29, 1990.
   Google Scholar
• Nagy, L.; Fogassy, E.; Tőke, L.; Ács, M.; Árvai, L.; Szabó, G. Resolution of alkali metal salts and lactones of racemic cis-2-hydroxycyclopent-4en-1-ylacetic acid with optically-active α-phenylethylamine. Hungarian Patent 177583, Jan. 10, 1978.
   Google Scholar
• Fogassy, E.; Ács, M. Process for producing 2-(4-hydroxyphenoxy)propionic acid enantiomers from enantiomer mixtures. Hungarian Patent 60226 Feb. 15, 1991
   Google Scholar
• Fogassy, E.; Simay, A.; Bergmann, J.; Faigl, F.; Birkás, E.; Mozsolits, K.; Szinnyei, É.; Török, Z.; Zolyomi, G.; Ács, M. Preparation of optically active isomers of 1-(4-fluorophenyl)-2-methylaminopropane by resolution with (R)-tartaric acid. Hungarian Patent 45963, Oct. 20, 1986.
   Google Scholar
• Fogassy, E.; Faigl, F.; Ács, M. Diastereomer salts of phenylalanine and N-acyl derivatives for the separation of optically active phenylalanine and N-acyl derivatives. WO Patent 8503932, Sep. 12, 1985.
   Google Scholar
• Nagy, L.; Fogassy, E.; Faigl, F.; Kozsda, É.; Csíz, L.; Csudor, I. Producing enantiomers of insecticidal cis- or trans-cyclopropanecarboxylic acid esters. Hungarian Patent 46649, Jan 8, 1987.
   Google Scholar
• Bálint, J.; Egri, G.; Vass, G.; Schindler, J.; Gajáry, A.; Friesz, A.; Fogassy, E. (2000) Resolution of the flumequine intermediate 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline. Tetrahedron: Asymmetry, 11 (3): 809.
   Web of Science ®Google Scholar
• Tóth, G.; Fogassy, E.; Ács, M.; Tőke, L.; Láng, T. (1983) Resolution of (±)​-​5-​ethyl-​1-​(3,​4-​dimethoxyphenyl)​-​6,​7-​dimethoxy-​4-​methyl-​5H-​2,​3-​benzodiazepine and the anomalous chiroptic behavior of the enantiomers. J. Het. Chem., 20 (3): 709.
   Web of Science ®Google Scholar
• Nemák, K.; Ács, M.; Jászay, Z. M.; Kozma, D.; Fogassy, E. (1996) Study of the diastereoisomers formed between (N-alkyl)-pipecolic acid-anilides and 2R,3R-tartaric acid or O,O-dibenzoyl-2R,3R-tartaric acid. Do the tartaric acids form molecular-complexes, instead of salts during optical resolutions? Tetrahedron, 52 (5): 1637.
   Web of Science ®Google Scholar
• Nemák, K.; Kozma, D.; Fogassy, E. (1996) Study of the mechanism of optical resolutions via diastereoisomeric salt formation part 4 - The role of the crystallization temperature in optical resolution of pipecolic acid xylidides. Mol. Cryst. Liq. Crys. A, 276: 31.
   Web of Science ®Google Scholar
• Nemák, K.; Ács, M.; Kozma, D.; Fogassy, E. (1997) Racemic compound formation-conglomerate formation: Part 4. Optical resolution and determination of the melting phase diagrams of 2,6-pipecoloxylidide and four 1-alkyl-2,6-pipecoloxylidides. J. Therm. Anal., 48 (3): 691.
   Web of Science ®Google Scholar
• Fogassy, E.; Török, Z.; Ács, M.; Bencsik, P.; Tóth, G.; Bernáth, G.; Minker, E.; Ecsery, Z.; Gera, L.; Minker, E. Resolution of 2-(3-chlorophenyl)-5,6-trimethylene-5,6-dihydropyrimidin-4(3H)one. Hungarian Patent 37130, Nov. 28, 1985.
   Google Scholar
• Fogassy, E.; Mészáros, Z.; Hermecz, I.; Vasvári, Á.; Horváth, Á.; Ács, M. Resolution of 4-oxo-6-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylicacid. Hungarian Patent 13416, Jun. 28, 1977
   Google Scholar