(Polyfluoro)silane-mediated generation of azomethine ylides from imines and their cycloaddition leading to N-heterocycles

Tetrahedron Letters

Volumn 44, Issue 8, 2003, Pages 1603-1606

  Komatsu, Mitsuo ^a   Okada, Hirofumi ^a   Yokoi, Seiji ^a   Minakata, Satoshi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

silylimine; 1,3 dipolar cycloaddition; Azomethine ylide; Fluorosilane; Pyrrolidine

Indexed keywords

(POLYFLUORO)SILANE; ALPHA(TRIMETHYLSILYL)IMINE; AZOMETHINE YLIDE; HETEROCYCLIC COMPOUND; IMINE; NITROGEN; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; ROOM TEMPERATURE;

EID: 0037450461     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00011-X     Document Type: Article

References (33)

1. Huisgen R. Padwa A. 1,3-Dipolar Cycloaddition Chemistry. 1:1984;1-176 John Wiley & Sons, New York.
2. For reviews, see: (a) Lown, J. W. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons: New York, 1984; Vol. 1, pp. 653-732;
3. (b) Vedejs, E.; West, F. G. Chem. Rev. 1986, 86, 941-955;
4. (c) Tsuge, O.; Kanemasa, S. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: San Diego, 1989; Vol. 45, pp. 231-349.
5. Vedejs E., Martinez G.R. J. Am. Chem. Soc. 101:1979;6452-6454.
6. Vedejs E., Martinez G.R. J. Am. Chem. Soc. 102:1980;7993-7994.
7. Vedejs E., West F.G. J. Org. Chem. 48:1983;4773-4774.
8. Padwa A., Haffmanns G., Tomas M. J. Org. Chem. 49:1984;3314-3322.
9. Vedejs E., Larsen S., West F.G. J. Org. Chem. 50:1985;2170-2174.
10. Tsuge O., Kanemasa S., Matsuda K. Chem. Lett. 1985;1411-1414.
11. Tsuge O., Kanemasa S., Matsuda K. J. Org. Chem. 51:1986;1997-2004.
12. Tsuge O., Hatta T., Kakura Y., Tashiro H., Maeda H., Kakehi A. Chem. Lett. 1997;945-946.
13. Achiwa K., Sekiya M. Chem. Lett. 1981;1213-1216.
14. Smith R., Livinghouse T. J. Org. Chem. 48:1983;1554-1555.
15. Livinghouse T., Smith R. J. Chem. Soc., Chem. Commun. 1983;210-211.
16. Achiwa K., Sekiya M. Tetrahedron Lett. 23:1982;2589-2592.
17. Imai N., Terao Y., Achiwa K. Heterocycles. 23:1985;1107-1110.
18. Achiwa K., Imai N., Motoyama T., Sekiya M. Chem. Lett. 1984;2041-2044.
19. Pearson W.H., Clark R.B. Tetrahedron Lett. 40:1999;4467-4471.
20. Tsuge O., Kanemasa S., Hatada A., Matsuda K. Chem. Lett. 1984;801-804.
21. Tsuge O., Kanemasa S., Yamada T., Matsuda K. Heterocycles. 23:1985;2489-2492.
22. Tsuge O., Kanemasa S., Hatada A., Matsuda K. Bull. Chem. Soc. Jpn. 59:1986;2537-2545.
23. Tsuge O., Kanemasa S., Yamada T., Matsuda K. J. Org. Chem. 52:1987;2523-2530.
24. Hosomi A., Miyashiro Y., Yoshida R., Tominaga Y., Yanagi T., Hojo M. J. Org. Chem. 55:1990;5308-5310.
25. Tominaga Y., Ogata K., Kohra S., Hojo M., Hosomi A. Tetrahedron Lett. 32:1991;5987-5990.
26. Terao Y., Aono M., Achiwa K. Heterocycles. 27:1988;981-1008.
27. Komatsu M., Ohno M., Tsuno S., Ohshiro Y. Chem. Lett. 1990;575-576.
28. Iyoda M., Sultana F., Komatsu M. Chem. Lett. 1995;1133-1134.
29. Ohno M., Komatsu M., Miyata H., Ohshiro Y. Tetrahedron Lett. 32:1991;5813-5816.
30. Washizuka K.-I., Minakata S., Ryu I., Komatsu M. Tetrahedron. 55:1999;12969-12976.
31. Komatsu M., Okada H., Akaki T., Oderaotoshi Y., Minakata S. Org. Lett. 4:2002;3505-3508.
32. 3v we could find the alternative method utilizing a fluorosilane and successfully apply the protocol to one-pot reaction from simple imines.
33. Derstine C.W., Smith D.N., Katzenellenbogen J.A. J. Am. Chem. Soc. 118:1996;8485-8486.