Synthesis of polyfunctional phosphorodithioates and structural analogues mediated by azetidinium ions and epoxides

Tetrahedron Letters

Volumn 44, Issue 16, 2003, Pages 3239-3243

  Jeziorna, Agata ^a   Heliński, Jan ^a   Krawiecka, Bozena ^a  

^a CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

Author keywords

Alkylation; Azetidines; Epoxides; Phosphorothioic acids and derivatives

Indexed keywords

AZETIDINE DERIVATIVE; EPOXIDE; N,N DIBENZYL 2,3 EPOXYPROPYLAMINE; PHOSPHORODITHIOIC ACID DERIVATIVE; PHOSPHORUS; UNCLASSIFIED DRUG;

ARTICLE; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0037436894     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00638-5     Document Type: Article

References (38)

1. Tanner D. Angew. Chem., Int. Ed. Engl. 50:1994;5775.
2. McCoull W., Davis F.A. Synthesis. 2000;1347. and references cited therein.
3. Almena J., Foubelo F., Yus M. Tetrahedron. 50:1994;5775.
4. Alcaide B., Almendros P., Aragocillo C., Selgado N.R. J. Org. Chem. 64:1999;9596.
5. Ungureanu I., Klotz P., Schoenfelder A., Mann A. J. Chem. Soc., Chem. Commun. 2001;958. and references cited therein.
6. Heliński J., Skrzypczyński Z., Michalski J. Tetrahedron Lett. 36:1995;9201.
7. Bakalarz A., Heliński J., Krawiecka B., Michalski J., Potrzebowski M.J. Tetrahedron. 55:1999;12211.
8. Bakalarz-Jeziorna A., Heliński J., Krawiecka B. J. Chem. Soc., Perkin Trans. 1. 2001;1086.
9. Jeziorna A., Heliński J., Krawiecka B. Synthesis. 2003;288.
10. For the preparation of 3-hydroxyazetidinium salts, see: (a) Gaertner, V. R. Tetrahedron Lett. 1966, 7, 4691; J. Org. Chem. 1967, 33, 2972;
11. J. Org. Chem. 1967, 33, 2972;
12. (b) Anderson, A. G., Jr.; Lok, R. J. Org. Chem. 1972, 37;
13. (d) Chatterjee, S. S.; Shoeb, A. Synthesis 1973, 153.
14. Hoffmann, H.; Schellenbeck, P. Chem. Ber. 1966, 99, 1134.
15. Buchwald S.L., Pliura D.H., Knowles J.R. J. Am. Chem. Soc. 106:1984;4916. and references cited therein.
16. Hamer N.K. J. Chem. Soc., Chem. Commun. 1968;1399.
17. Gay D.C., Hamer N.K. J. Chem. Soc. B. 1970;1123.
18. Nuretdinova O.N., Guseva F.F., Arbuzov B.A. Izv. Akad. Nauk SSSR, Ser. Khim. 1976;2625.
19. Nuretdinova O.N., Guseva F.F. ibid. 1980;2594.
20. Tanaka K., Uneme H., Ono N., Kaji A. Chem. Lett. 1979;1039.
21. Dybowski P., Skowrońska A. Tetrahedron Lett. 32:1991;4385.
22. Dybowski P., Skowrońska A. Synthesis. 1997;284.
23. Concellón J.M., Bernad P.L., Pérez-Andrés J.A. Tetrahedron Lett. 41:2000;1231.
24. Kudelska W., Michalska M. Tetrahedron. 42:1986;629.
25. Kudelska W., Michalska M. Tetrahedron. 37:1981;2989.
26. Michalska M., Brzezinska E., Lipka P. J. Am. Chem. Soc. 113:1991;7945.
27. Yadew L.D., Kapoor R. Synthesis. 2002;1502.
28. abstract
29. 31P NMR spectra were recorded periodically. In addition to salts 1a and 2a-d azetidinium salts given in Table 2 and 2 given in Table 3 were used.
30. Herschlag D. J. Am. Chem. Soc. 116:1994;11631.
31. Ora M., Järvi J., Oivanen M., Lönnberg H. J. Org. Chem. 65:2000;2651.
32. Hall H.K. J. Am. Chem. Soc. 79:1957;5439.
33. Campbell K.N., Fatora F.C., Cambell B.K. Can. J. Chem. 38:1960;2109.
34. Kudelska W., Michalska M. Carbohydr. Res. 1980;83.
35. Kudelska W., Michalska M. Ibid. 90:1981;1.
36. Guivisdalski P.N., Bittman R. J. Am. Chem. Soc. 111:1989;3077.
37. 3), 66.60 (CHOH), 126.63, 127.63, 128.25, 128.50, 129.04, 129.30 (aromatic), 136.95 (C-ipso).