Phenylaziridine as a 1,3-dipole. Application to the synthesis of functionalized pyrrolidines

Tetrahedron Letters

Volumn 40, Issue 29, 1999, Pages 5315-5318

  Ungureanu, Ioana ^a   Bologa, Cristian ^b   Chayer, Saïd ^a   Mann, André ^a  

^a Laboratoire de Pharmacochimie   (France)

^b UNIVERSITY OF BUCHAREST   (Romania)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; SYNTHESIS;

EID: 0033575451     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01002-3     Document Type: Article

References (25)

1. Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599-619.
2. Toshimitsu, A.; Abe, H.; Hirosawa, C.; Tamao, K. J. Chem. Soc., Perkin Trans, 1 1994, 3465-3471.
3. Kozikowski, A. P.; Ishida, H.; Isobe, K. J. Org. Chem. 1979, 44, 2788-2790.
4. Ibuka, T.; Schoenfelder, A.; Bildstein, P.; Mann, A. Synth. Commun. 1995, 25, 1777-1782.
5. Schneider, M. R.; Taddei, M.; Mann, A. Tetrahedron Lett. 1996, 37, 8493-8496.
6. Schneider, M. R.; Klotz, P.; Ungureanu, I.; Mann, A.; Wermuth, C. G. Tetrahedron Lett. 1999, 40, 3873-3876.
7. Fleming, I.; Langley, A. J. J. Chem. Soc., Perkin Trans. 1 1981, 1421-1423.
8. Effenberger, F.; Gleiter, R. Chem. Be. 1964, 97, 1576-1583.
9. Kaluzia, Z.; Abramski, W.; Belzecki, C.; Grodner, J.; Mostowicz, D.; Urbanski, R.; Chmielewski, M. Synlett 1994, 539-541.
10. Iwashita, T.; Kusumi, T.; Kakisawa, H. J. Org. Chem. 1982, 47, 230-233.
11. Cardona, F.; Valenza, S.; Goti, A.; Brandi, A. Tetrahedron Lett. 1997, 38, 8097-8100.
12. Paul, R.; Tchelitcheff, S. Bull. Soc. Chim. Fr. 1952, 672-678.
13. Franck, R. W.; John, T. V. J. Org. Chem. 1980, 45, 1170-1172.
14. Baudelle, R.; Melnyk, P.; Deprez, B.; Tartar, A. Tetrahedron 1998, 54, 4125-4140.
15. Leblanc, Y.; Fitzimmons, B. J.; Springer, J. P.; Rokach, J. J. Am. Chem. Soc. 1989, 111, 2995-3000.
16. Griengl, H.; Bleikolm, A. Liebigs Ann. Chem. 1976, 1783-1791.
17. +).
18. The X-ray structures and coordinates for 4a and 4b have been submitted to the Cambridge Crystallographic Database under the following codes CCDC 121746 (4b) and CCDC 121747 (4a).
19. Ahman, J.; Somfai, P. Tetrahedron 1992, 48, 9537-9544.
20. Ahman, J.; Somfai, P. J. Chem. Soc., Perkin Trans. 1 1994, 1079-1082.
21. Renaud, P.; Seebach D. Helv. Chem. Acta 1986, 69, 1704-1710.
22. +).
23. +).
24. For an illustrative example see: Snyder, S. E.; Aviles-Garay, F. A.; Chakraborti, R.; Nichols, D. E.; Watts, V. J.; Mailhman, R. B. J. Med. Chem. 1995, 38, 2395-2409.
25. For a review on the kainoids see: Parsons, A. F. Tetrahedron 1996, 52, 4149-4174.