Use of Selenium-Bound Resin for the Solid-Phase Synthesis of Substituted Isoxazolyl-Substituted (E)-Olefins

Organic Letters

Volumn 5, Issue 24, 2003, Pages 4649-4652

  Huang, Xian ^a,b   Xu, Wel Ming ^a  

^a ZHEJIANG UNIVERSITY   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; BROMIDE; ISOXAZOLE DERIVATIVE; POLYSTYRENE; RESIN; SELENIUM DERIVATIVE;

ALKYLATION; ARTICLE; CYCLOADDITION; SOLID; SYNTHESIS;

EID: 0346150273     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035816u     Document Type: Article

References (42)

1. (a) Guilliier, F.; Orain, D.; Bradley, M. Chem. Rev. 2000, 100, 2091-2157.
2. (b) James, I. W. Tetrahedron 1999, 55, 4855-4946.
3. (c) Sammelson, R. E.; Kurth, M. J. Chem. Rev. 2001, 137-202.
4. (d) Czarnik, A. W. Solid-Phase Organic Synthesis; Wiley: New York, 2001; Vol. 1
5. (e) Nicolaou, K. C.; Hanko, R.; Hartwig, W. Handbook of Combinatorial Chemistry; Wiley-VCH: Weinheim, Germany, 2002.
6. (f) Dolle, R. E. J. Comb. Chem. 2002, 4, 369-418.
7. (g) Dolle, R. E. J. Comb. Chem. 2001, 3, 477-517.
8. Van Maarseveen, J. H. Comb. Chem. High Throughput Screening 1998, 1, 185-214.
9. (a) Rowley, M.; Broughton, H. B.; Collins, I.; Baker, R.; Emms, F.; Marwood, R.; Patel, S.; Patel, S.; Ragan, C. I.; Freedman, S. B.; Leeson, P. D. J. Med. Chem. 1996, 39, 1943-1945.
10. (b) Simoni, D.; Roberti, M.; Invidiata, F. P.; Rondanin, R.; Baruchello, R.; Malagutti, C.; Mazzali, A.; Rossi, M.; Grimaudo, S.; Capone, F.; Dusonchet, L.: Meli, M.; Raimondi, M. V.; Landino, M.; D'Allesandro, N.; Tolomeo, M.; Arindam, D.; Lu, S.; Benbrook, D. M. J. Med. Chem. 2001, 44, 2308-2318.
11. (c) Wityak, J.; Sielecki, T. M.; Pinto, D. J.; Emmett, G.; Sze, J. Y.; Liu, J.; Tobin, A. E.; Wang, S.; Jiang, B.; Ma, P.; Mousa, S. A.; Olson, R. E.; Wexler, R. R. J. Med. Chem. 1997, 40, 50-60.
12. (a) Koiowski, A. P. Acc. Chem. Res. 1984, 17, 410-416.
13. (b) Padwa, A.; Pearson, W. H. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; The Chemistry of Heterocyclic Compounds, Vol. 59; John Wiley & Sons: New York, 2002.
14. For recent reviews, see: (a) Franzen, R. G. J. Comb. Chem. 2000, 2, 195-214. (b) Dowald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, Germany, 2002; Chapter 15.
15. For recent reviews, see: (a) Franzen, R. G. J. Comb. Chem. 2000, 2, 195-214. (b) Dowald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, Germany, 2002; Chapter 15.
16. (a) Shen, D. M.; Shu, M.; Chapman, K. T. Org. Lett. 2000, 2, 2789-2792.
17. (b) Marzinzik, A. L.; Felder, E. R. Tetrahedron Lett. 1996, 37, 1003-1006.
18. (a) Kurth, M. J.; Miller, R. B.; Lorsbach, A. B. J. Org. Chem. 1996, 61, 8716-8717.
19. (b) Kurth, M. J.; Ahlberg Randall, L. A.; Takenouchi, K. J. Org. Chem. 1996, 61, 8755-8761.
20. (c) Kurth, M. J.; Kantorowski, E. J. J. Org. Chem. 1997, 62, 6797-6803.
21. (a) Shankar, B. B.; Yang, D. Y.; Girton, S.; Ganguly, A. K. Tetrahedron Lett. 1998, 39, 2447-2448.
22. (b) Cheng, J. F.; Mjalli, M. M. Tetrahedron Lett. 1998, 39, 939-942.
23. (c) Zou, N.; Jiang, B. J. Comb. Chem. 2000, 2, 6-7.
24. Cheng, W. C.; Wong, M.; Olmstead, M. M.; Kurth, M. J. Org. Lett. 2002, 4, 741-744.
25. Michels, R.; Kato, M.; Heitz, W. Makromol. Chem. 1976, 177, 2311-2317.
26. (a) Nicolaou, K. C.; Pastor, J.; Barluenga, S.; Winssinger, N. Chem. Commun. 1998, 1947-1948.
27. (b) Nicolaou, K. C.; Pfefferkorn, J. A.; Roecker, A. J.; Cao, G. Q.; Barluenga, S.; Mitchell, H. J. J. Am. Chem. Soc. 2000, 122, 9939-9953.
28. (c) Ruhland, T.; Andersen, K.; Pedersen, H. J. Org. Chem. 1998, 63, 9204-9211.
29. (d) Nicolaou, K. C.; Pfefferkorn, J. A.; Cao, G. Angew. Chem., Int. Ed. 2000, 112, 750-755.
30. (e) Zaragoza, F. Angew. Chem., Int. Ed. 2000, 39, 2077-2079.
31. (f) Fujita, K.; Taka, H.; Oishi, A.; Ikeda, Y.; Taguchi, Y.; Fujie, K.; Saeki, T.; Sakuma, M. Synlett 2000, 1509-1511.
32. (a) Huang, X.; Xu, W. M. Tetrahedron Lett. 2002, 43, 5495-5497.
33. (b) Qian, H.; Huang, X. Synlett 2001, 12, 1913-1916.
34. (c) Huang, X.; Sheng, S. R. Tetrahedron Lett. 2001, 42, 9035-9037.
35. (d) Qian, H.; Huang, X. Tetrahedron Lett. 2002, 43, 1059-1061.
36. (e) Huang, X.; Sheng, S. R. J. Comb. Chem. 2003, 5, 273-277.
37. (f) Qian, H.; Huang, X. J. Comb. Chem. 2003, 5, 569-576.
38. (a) Clive, D. L. J. Tetrahedron 1978, 34, 1049-1095.
39. (b) Wirth, T. Organoselenium Chemistry; Springer-Verlag Press: Berlin, Heideberg, Germany, 2000.
40. For reviews, see the following: (a) Padwa, A. 1,3-Dipolar Cycloaddition Chemistry; John Wiley & Sons: New York, 1984. (b) Torsell, K. G. B. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis; VCH: New York, 1988.
41. For reviews, see the following: (a) Padwa, A. 1,3-Dipolar Cycloaddition Chemistry; John Wiley & Sons: New York, 1984. (b) Torsell, K. G. B. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis; VCH: New York, 1988.
42. Reich, H. J. J. Org. Chem. 1975, 40, 2570-2572.