Crystal and molecular structure of the levorotatory (1R,2S)-ephedrinium (S)-t-butylsulfinylacetate: A definitive proof of the absolute configuration of enantiomeric t-butyl methyl sulfoxides

Tetrahedron Asymmetry

Volumn 9, Issue 7, 1998, Pages 1171-1178

  Drabowicz, Józef ^a   Dudziński, Bogdan ^a   Mikołajczyk, Marian ^a   Wieczorek, Michał W ^b   Majzner, Wiesław R ^b  

^a CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

^b LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EPHEDRINE; EPHEDRINIUM TERT BUTYLSULFINYLACETATE; SULFOXIDE; TERT BUTYL METHYL SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; ENANTIOMER; OPTICAL ROTATION; PRIORITY JOURNAL; STRUCTURE ANALYSIS; X RAY;

EID: 0345267349     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00110-4     Document Type: Article

References (26)

1. Mislow, K.; Green, M. M.; Laur, P.; Melillo, J. P.; Simmons, T.; Ternay, A. L. J. Am. Chem. Soc., 1965, 87, 1958.
2. Axelrod, M.; Bickert, P.; Goldstein, M. L.; Green, M. M.; Kjaer, A.; Mislow, K. Tetrahedron Lett., 1968, 3249.
3. (a) Fernandez, I.; Khiar, N.; Llera, J. M.; Alcudia, F. J. Org. Chem., 1992, 57, 6789.
4. (b) Khiar, N.; Fernandez, I.; Alcudia, F. Tetrahedron Lett., 1994, 35, 5719.
5. Evans, D. A.; Faul, M. M.; Colombo, L.; Bisaha, J. J.; Clardy, J.; Cherry, D. J. Am. Chem. Soc., 1992, 11, 5977.
6. (a) Oae, S.; Yokoyama, M.; Kisi, M.; Furukawa, N. Tetrahedron Lett., 1968, 4131.
7. (b) Maricich, T. J.; Hoffman, V. L. Tetrahedron Lett., 1972, 5309.
8. (c) Maricich, T. J.; Hoffman, V. L. J. Am. Chem. Soc., 1974, 96, 7770.
9. (d) Christensen, B. W.; Kjaer, A. J. Chem. Soc., Chem. Commun., 1969, 934.
10. (e) Christensen, B. W. J. Chem. Soc., Chem. Commun., 1971, 597.
11. (f) Mikołajczyk, M.; Drabowicz, J. J. Chem. Soc., Chem. Commun., 1974, 775.
12. (g) Kresze, G.; Rössert, M. Angew. Chem., 1978, 90, 61; Angew. Chem. Int. Ed. Eng., 1978, 17, 64.
13. (g) Kresze, G.; Rössert, M. Angew. Chem., 1978, 90, 61; Angew. Chem. Int. Ed. Eng., 1978, 17, 64.
14. (h) Drabowicz, J.; Bujnicki, B.; Mikołajczyk, M. J. Org. Chem., 1981, 46, 2788.
15. (i) Schwöbel, A.; Kresze, G.; Perez, M. A. Tetrahedron Lett., 1982, 23, 1243.
16. (j) Mikołajczyk, M.; Drabowicz, J.; Bujnicki, B. Tetrahedron Lett., 1985, 26, 5699.
17. (k) Drabowicz, J.; Mikołajczyk, M. Tetrahedron Lett., 1985, 26, 5703.
18. (l) Colonna, S.; Germinario, G.; Manfredi, A.; Stirling, C. J. M. J. Chem. Soc., Perkin Trans. I, 1988, 1695.
19. Drabowicz, J.; Dudziński, B.; Mikołajczyk, M. J. Chem. Soc., Chem. Commun., 1992, 1500.
20. Drabowicz, J.; Dudziński, B.; Mikołajczyk, M. Tetrahedron: Asymmetry, 1992, 3, 1231.
21. Rebiere, F.; Samuel, O.; Ricard, L.; Kagan, H. B. J. Org. Chem., 1991, 56, 5991.
22. Rogers, D. Acta Cryst., 1981, A37, 734.
23. Frenz, B.A. SDP - Structure Determination Package, Enraf-Nonius, Delft, Holland, 1984.
24. Sheldrick, G. M.; Krüger, G. M.; Goddard, R. SHELXS-86. Crystallographic Computing 3, Oxford University Press, 1985, p. 175.
25. SHELXT PC, Release 4.1 (May 1990). Siemens Analytical X-Ray Instruments, Inc., Madison, WI 53719, USA.
26. Cambridge Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, UK.