Unconventional preparation of racemic crystals of isopropyl 3,3,3-trifluoro-2-hydroxypropanoate and their unusual crystallographic structure: The ultimate preference for homochiral intermolecular interactions

Chemical Communications

Volumn 49, Issue 4, 2013, Pages 373-375

  Aceña, José Luis ^a   Sorochinsky, Alexander E ^a,b   Katagiri, Toshimasa ^c   Soloshonok, Vadim A ^a,b  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b BASQUE FOUNDATION FOR SCIENCE   (Spain)

^c OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DIMER; ISOPROPYL 3,3,3 TRIFLUORO 2 HYDROXYPROPANOATE; OLIGOMER; PROPIONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CHEMICAL REACTION; CRYSTALLOGRAPHY; ENANTIOMER; HYDROGEN BOND; MOLECULAR INTERACTION; RACEMIC MIXTURE; SUBLIMATION REACTION;

EID: 84870873368     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c2cc37491a     Document Type: Article

References (46)

1. H. Ueki, M. Yasumoto, V. A. Soloshonok, Tetrahedron 2010 21 1396
2. J. Han, D. J. Nelson, A. E. Sorochinsky, V. A. Soloshonok, Curr. Org. Synth. 2011 8 310
3. V. A. Soloshonok, C. Roussel, O. Kitagawa, A. E. Sorochinsky, Chem. Soc. Rev. 2012 41 4180
4. V. A. Soloshonok, Angew. Chem., Int. Ed. 2006 45 766
5. V. A. Soloshonok, D. O. Berbasov, Chem.Today 2006 24 44
6. J. Jacques, S. H. Wilen and A. Collet., Enantiomers, Racemates and Resolution, Wiley-Interscience, New York, 1994
7. E. L. Eliel, S. H. Wilen and L. N. Mander., Stereochemistry of Organic Compounds, Wiley-Interscience, New York, 1994
8. Y. Mastai, A. Volkel, H. Colfen, J. Am. Chem. Soc. 2008 130 2426
9. D. Kozma, C. Kassai, F. Fogassy, Tetrahedron Lett. 1995 36 3245
10. V. A. Soloshonok, H. Ueki, M. Yasumoto, S. Mekala, J. S. Hirschi, D. A. Singleton, J. Am. Chem. Soc. 2007 129 12112
11. R. H. Perry, C. Wu, M. Nefliu, G. Cooks, Chem. Commun. 2007 1071
12. S. P. Fletcher, R. B. C. Jagt, B. L. Feringa, Chem. Commun. 2007 2587
13. A. Bellec, J. C. Guillemin, Chem. Commun. 2010 46 1482
14. A. Bellec, J. C. Guillemin, J. Fluorine Chem. 2010 131 545
15. V. A. Basiuk, T. Y. Gromovoy, A. A. Chuiko, V. A. Soloshonok, V. P. Kukhar, Synthesis 1992 449
16. M. Yasumoto, H. Ueki, V. A. Soloshonok, J. Fluorine Chem. 2010 131 266
17. M. Yasumoto, H. Ueki, V. A. Soloshonok, J. Fluorine Chem. 2010 131 540
18. S. Ogawa, T. Nishimine, E. Tokunaga, S. Nakamura, N. Shibata, J. Fluorine Chem. 2010 131 521
19. M. Takahashi, H. Tanabe, T. Nakamura, H. Kuribara, T. Yamazaki, O. Kitagawa, Tetrahedron 2010 66 288
20. T. Nakamura, K. Tateishi, S. Tsukagoshi, S. Hashimoto, S. Watanabe, V. A. Soloshonok, J. L. Aceña, O. Kitagawa, Tetrahedron 2012 68 4013
21. V. A. Soloshonok, D. O. Berbasov, J. Fluorine Chem. 2006 127 597
22. C. Girard, H. B. Kagan, Angew. Chem., Int. Ed. 1998 37 2922
23. C. Girard, H. B. Kagan, Can. J. Chem. 2000 78 816
24. R. Noyori, S. Suga, H. Oka, M. Kitamura, Chem. Rec. 2001 1 85
25. T. Katagiri, C. Yoda, K. Furuhashi, K. Ueki, T. Kubota, Chem. Lett. 1996 115
26. T. Katagiri, K. Uneyama, Chem. Lett. 2001 1330
27. T. Katagiri, S. Takahashi, A. Tsuboi, M. Suzaki, K. Uneyama, J. Fluorine Chem. 2010 131 517
28. S. Takahashi, T. Jukurogi, T. Katagiri, K. Uneyama, CrystEngComm 2006 8 320
29. R. S. Boethling and D. Mackay., Handbook of Property Estimation Methods for Chemicals, Lewis Publishers, Boca Raton, 2000, Ch. 1 and 2M.
30. Yasumoto, H. Ueki, T. Ono, T. Katagiri, V. A. Soloshonok, J. Fluorine Chem. 2010 131 535
31. L. A. Paquette, C. J. Lau, J. Org. Chem. 1987 52 1634
32. O. Wallach, Liebigs Ann. Chem. 1895 286 90
33. C. P. Brock, W. B. Schweizer, J. D. Dunitz, J. Am. Chem. Soc. 1991 113 9811
34. S. Takahashi, T. Katagiri, K. Uneyama, Chem. Commun. 2005 3658
35. P. Bravo, A. Farina, M. Frigerio, S. Valdo Meille, F. Viani, V. A. Soloshonok, Tetrahedron 1994 5 987
36. V. A. Soloshonok, T. Ono, Tetrahedron 1996 52 14701
37. V. A. Soloshonok, A. G. Kirilenko, S. V. Galushko, V. P. Kukhar, Tetrahedron Lett. 1994 35 5063
38. A. E. Sorochinsky, V. A. Soloshonok, J. Fluorine Chem. 2010 131 127
39. T. Katagiri, S. Yamaji, M. Handa, M. Irie, K. Uneyama, Chem. Commun. 2001 2054
40. T. Katagiri, Y. Fujiwara, S. Takahashi, N. Ozakia, K. Uneyama, Chem. Commun. 2002 986
41. V. A. Soloshonok, D. V. Avilov, V. P. Kukhar, L. Van Meervelt, N. Mischenko, Tetrahedron Lett. 1997 38 4903
42. V. A. Soloshonok, A. G. Kirilenko, N. A. Fokina, S. V. Galushko, V. P. Kukhar, V. K. Svedas, G. Resnati, Tetrahedron 1994 5 1225
43. V. A. Soloshonok, D. V. Avilov, V. P. Kukhar, Tetrahedron 1996 7 1547
44. V. A. Soloshonok, A. D. Kacharov, D. V. Avilov, K. Ishikawa, N. Nagashima, T. Hayashi, J. Org. Chem. 1997 62 3470
45. T. S. Balaban, A. D. Bhise, G. Bringmann, J. Bürck, C. Chappaz-Gillot, A. Eichhöfer, D. Fenske, D. C. G. Götz, M. Knauer, T. Mizoguchi, D. Mössinger, H. Rösner, C. Roussel, M. Schraut, H. Tamiaki, N. Vanthuyne, J. Am. Chem. Soc. 2009 131 14480
46. I. Higler, L. Grave, E. Breuning, W. Verboom, F. D. Jong, T. M. Fyles, D. N. Reinhoudt, Eur. J. Org. Chem. 2000 1727