Enantioselective synthesis of (S)-(-)-3-amino-5-(mrpholinomethyl)-1,3-oxazolidin-2-one. An intramolecular competition for oxirane versus azetidine ring formation

Polish Journal of Chemistry

Volumn 70, Issue 7, 1996, Pages 891-900

  Achmatowicz, O ^a   Malinowska, I ^a   Wisniewska A ^a   Galdecki Z ^b   Fruzinski A ^b  

^a INDUSTRIAL CHEMISTRY RESEARCH INSTITUTE   (Poland)

^b LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Chiral synthons; Enantioselectivity; Spirane; Synthesis; X ray analysis

Indexed keywords

EID: 0030545442     PISSN: 01375083     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (21)

1. Negwer M., Organic-chemical Drugs and their Synonyms, 7th Ed., Academic Verlag GmbH, Berlin, 1994.
2. Ref. 1, Vol. I, p. 765.
3. Kessler H.J., Rufer C. and Schwarz K., Eur. J. Med. Chem.-Chim. Ther., 11, 19 (1976).
4. a. Sheldon R.A., Chirotechnology: Industrial Synthesis of Optically Active Compounds, Marcel Dekker, New York, 1993.
5. b. Drugs Stereochemistry: Analytical Methods and Pharmacology, Weiner I.W., (Ed.), Marcel Dekker, New York, 1993.
6. c. Stinson S.C., Chemical and Eng. News, Oct. 9, 1995, p. 44.
7. Świrska A., Acta Polon. Pharm., 19, 317 (1962).
8. Hanson R.H., Chem. Rev., 91, 437 (1991).
9. Jung M.E. and Show T.J., J. Am. Chem. Soc., 102, 6304 (1980).
10. Murthy V.S., Gaitaude A.S. and Ras S.P., Synthetic Common., 23, 285 (1983).
11. Davies D.E. and Storr R.C., in Comprehensive Heterocyclic Chemistry, Katritzky A.R. (Ed.), Vol. 7, Pergamon Press, Oxford, 1984, p. 237.
12. Handbook of Heterocyclic Chemistry, Katritzky A.R. (Ed.), Pergamon Press, Oxford, 1985, p. 393.
13. Zacharis H.M. and Trefonas L.M., J. Am. Chem. Soc., 93, 2935 (1971).
14. Kliegel W., Retting S.J. and Trotter J., Can. J. Chem., 66, 377 (1988).
15. Duax W.L. and Norton D.A., Atlas of Steroid Structures, New York, Plenum Press, 1975, p. 16.
16. Eliel E.L. and Witen S.H., Stereochemistry of Organic Compounds, John Wiley and Sons, Inc., New York, 1994, p. 756.
17. a. Tsuda Y., Yoshimoto K. and Nishihawa T., Chem. Pharm. Bull., 12, 3593 (1961).
18. b. Baldwin J.J., Raab A., Mensler K., Arison B.H. and McClure D.E., J. Org. Chem., 43, 1978, 4876 (1978).
19. Sheldrick G.M., SHELXTL PC version 41. An integrated System for Solving, Refining and Displaying Crystal Structures form Diffraction Data, Siemens Analytical X-ray Instruments, Inc., Madison, USA, 1990.
20. Vickovic J., CSU-Crystal Structure Utility. Program for Geometrical Calculations. University of Zagreb, Yugoslavia, 1988.
21. Nardelli M., Comput. Chem., 1983, 7, 95.