Lanthanide triflate-catalyzed 1,3-dipolar cycloaddition reactions of polymer-supported nitrones with alkenes for the preparation of diverse 2- isoxazoline derivatives

Tetrahedron Letters

Volumn 39, Issue 50, 1998, Pages 9211-9214

  Kobayashi, Shu ^a   Akiyama, Ryo ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

2 ISOXAZOLINE DERIVATIVE; ALKENE; KETONE; LANTHANIDE; NITRIC ACID DERIVATIVE; POLYMER;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; SYNTHESIS;

EID: 0032506569     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02100-5     Document Type: Article

References (31)

1. 1 (a) Zang, L. -H.; Chung, J. C.; Costello, T. D.; Valvis, L; Ma, P.; Kauffman, S.; Ward, R. J. Org. Chem. 1997, 62, 2466-2470.
2. (b) Zang, L. -H.; Anzalone, L.; Ma, P.; Storace, L.; Ward, R. Tetrahedron Lett. 1996, 37, 4455-4458.
3. (c) Wityak, J.; Sielecki, T. M.; Pinto, D. J.; Emmett, G.; Sze, J. Y.; Liu, J.; Tobin, A. E.; Wang, S.; Jinag, B.; Ma, P.; Mousa, S. A.; Wexler, R. R.; Olson, R. E. J. Med. Chem. 1997, 40, 1292.
4. (d) Wityak, J.; Sielecki, T. M.; Pinto, D. J.; Emmett, G.; Sze, J. Y.; Liu, J.; Tobin, A. E.; Wang, S.; Jinag, B.; Ma, P.; Mousa, S. A.; Wexler, R. R.; Olson, R. E. J. Med. Chem. 1997, 40, 50-60.
5. 2 Groutas, W. C.; Venkataman, R.; Chong, L. S.; Yoder, J. E.; Epp, J. B.; Stanga, M. A.; Kim, E. -H. Bioorg. Med. Chem. 1995, 3, 125-128.
6. 3 Padwa, A. 1,3-Dipolar Cycloaddition Chemistry, John Wiley & Sons: New York, 1984, Vols. 1 and 2.
7. 4 Torssell, K. B. G. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis, VCH: Weinheim, 1988.
8. 5 (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555, and references cited therein.
9. (b) Révész, L.; Bonne, F.; Manning, U.; Zuber, J. -F. Bioorg. Med. Chem. Lett. 1998, 8, 405-408.
10. (c) Fantauzzi, P. P.; Yager, K. M. Tetrahedron Lett. 1998, 39, 1291-1294.
11. (d) Breitenbucher, J. G.; Johnson, C. R.; Haight, M.; Phelan, J. C. Tetrahedron Lett. 1998, 39, 1295-1298.
12. (e) Hamper, B. C.; Kolodziej, S. A.; Scates, A. M.; Smith, R. G.; Cortez, E. J. Org. Chem. 1998, 63, 708-718.
13. (f) Hone, N. D.; Davies, S. G.; Taylor, S. L.; Baxter, A. D. Tetrahedron Lett. 1998, 39, 897-900.
14. (g) Bhalay, G.; Blaney, P.; Palmer, V. H.; Baxter, A. D. Tetrahedron Lett. 1997, 38, 8375-8378.
15. (h) Scialdone, M. A. Tetrahedron Lett. 1996, 37, 8141-8144.
16. (i) Kobayashi, S.; Moriwaki, M.; Akiyama, R.; Suzuki, S.; Hachiya, I. Tetrahedron Lett. 1996, 37, 7783-7786.
17. (j) Tortolani, D. R.; Biller, S. A. Tetrahedron Lett. 1996, 37, 5687-5690.
18. (k) Kobayashi, S.; Hachiya, I.; Suzuki, S.; Moriwaki, M. Tetrahedron Lett. 1996, 37, 2809-2812.
19. 6 (a) Shankar, B. B.; Yang, D. Y.; Ganguly, A. K. Tetrahedron Lett. 1998, 39, 2447-2448.
20. (b) Cheng, J. -H.; Mjalli, A. M. M. Tetrahedron Lett. 1998, 39, 939-942.
21. 7 Haap, W. J.; Kaiser, D.; Walk, T. B.; Jung, W. G. Tetrahedron 1998, 54, 3705-3724.
22. 8 Intramolecular 1,3-dipolar cycloaddition on the solid-phase was reported. Beebe, X.; Chiappari, C. L.; Olmstead, M. M.; Kurth, M. J.; Schore, N. E. J. Org. Chem. 1995, 60, 4204-4212.
23. 9 DeGrado, W. F.; Kaiser, E. T. J. Org. Chem. 1980, 45, 1295-1300.
24. 10 Kawase, M.; Kikugawa, Y. J. Chem. Soc. Perkin Trans. 1 1979, 643-645.
25. 11 Ruhland, B.; Bahandari, A.; Gordon, E. M.; Gallop, M. A. J. Am. Chem. Soc. 1996, 118, 253-253.
26. 12 Kobayashi, S.; Akiyama, R.; Furuta, T.; Moriwaki, M. Molecules Oneline 1998, 2, 35-39.
27. 13 Kobayashi, S; Akiyama, R.; Kawamura, M.; Ishitani, H. Chem. Lett. 1997, 1039-1040.
28. 14 (a) Oikawa, Y.; Yoshioka, T. Tetrahedron Lett. 1982, 23, 885-888.
29. (b) Li, P.; Gi, H. -J.; Sun, L.; Zhao, K. J. Org. Chem. 1998, 63, 366-369.
30. 15 Nonpolymer-supported aliphatic nitrones are known to be unstable and sometimes difficult to employ in 1,3-dipolar cycloadditions.
31. 16 Kobayashi, S.; Kawamura, M. J. Am. Chem. Soc. 1998, 120, 5840-5841.