Unusual enantiomeric resolution phenomenon observed upon recrystallization of a racemic compound

Angewandte Chemie (International Edition in English)

Volumn 35, Issue 20, 1996, Pages 2372-2374

  Ushio, Takanori ^b   Tamura, Rui ^a   Takahashi, Hiroki ^a   Azuma, Nagao ^c   Yamamoto, Keiji ^d  

^a Grad Sch Environ Earth Sci H   (Japan)

^b TAIHO PHARMACEUTICAL CO LTD   (Japan)

^c EHIME UNIVERSITY   (Japan)

^d CHIBA UNIVERSITY   (Japan)

Author keywords

Crystallization; Enantiomeric resolution; Mixed crystals; Racemates

Indexed keywords

EID: 0030472723     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199623721     Document Type: Article

References (14)

1. L. Pasteur, Ann. Chim. Phys. 1848, 24, 442.
2. M. Gernez, C. R. Hebd. Seances Acad. Sci. 1866, 63, 843.
3. a) J. Jacques, A. Collet, S. H. Wilen, Enantiomers, Racemates and Resolutions, Wiley, New York, 1981, p. 217;
4. b) A. Collet, M.-J. Brienne, J. Jacques, Chem. Rev. 1980, 80, 215.
5. P. Newman, Optical Re solution Procedures for Chemical Compounds, Vol. 1-3, Optical Resolution Information Center, New York, 1978, 1981, 1984.
6. F. Toda, Top. Curr. Chem. 1987, 140, 43.
7. Asymmetric Synthesis, Vol. 5 (Ed.: J. D. Morrison), Academic Press, Orlando, FL, USA, 1985.
8. K. Mori, Y. Funaki, Tetrahedron 1988, 41, 2369.
9. Chromatographic Chiral Separations (Eds.: M. Zief, L. J. Crane), Marcel Dekker, New York, 1988.
10. A. Koda, Y. Yanagihara, N. Matsuura, Agents Actions 1991, 34, 369.
11. T. Ushio, K. Yamamoto, J. Chromatogr. A 1994, 684, 235.
12. 3, R = 0.044, Rw = 0.042. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-179-107. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Telefax: Int. code +(1223) 336-033; e-mail: teched@chemcrys.cam.ac.uk).
13. Polymorphism between the crystals of the racemic compound crystal and racemic mixed crystals is quite rare, see ref. [3], p. 137. For polymorphyism between racemic compounds and conglomerates, see M. Leclercq, A. Collet, J. Jacques, Tetrahedron 1976, 32, 821; E. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994, p. 161.
14. Polymorphism between the crystals of the racemic compound crystal and racemic mixed crystals is quite rare, see ref. [3], p. 137. For polymorphyism between racemic compounds and conglomerates, see M. Leclercq, A. Collet, J. Jacques, Tetrahedron 1976, 32, 821; E. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994, p. 161.