Auxiliary controlled intramolecular 1,3-dipolar cycloaddition reactions of Chiral Azomethine Ylides

Turkish Journal of Chemistry

Volumn 24, Issue 1, 2000, Pages 59-66

  Doǧan, Özdemir ^a   Garner, Philip P ^b  

^a MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

^b NONE

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EID: 0034345462     PISSN: 13000527     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (46)

1. Reviews of azomethine ylide chemistry: (a) Lown, W. J. In 1,3-Dipolar Cycloaddition Chemistry; Vol. I. Padwa, A., Ed.; Wiley: New York, 1984;
2. (b) Tsuge, O.; Kanemasa, S. Adv. Heterocycl. Chem. 45, 231 (1989).
3. (a) Garner, P.; Ho, W. B.; Shin, H. J. Am. Chem. Soc. 114, 2762 (1992).
4. (b) Kraus, G. A.; Nagy, J. O. Tetrahedron 41, 3537 (1985).
5. DeShong, P.; Kell, D. A. Tetrahedron Lett. 27 (1986).
6. DeShong, P.; Kell, D. A.; Sidler, D. R. J. Org. Chem. 50, 2309 (1985).
7. (e) Sisko, J.; Weinreb, S. M. Ibid. 56, 3210 (1991).
8. (f) Henke, B. R.; Kouklis, A. J.; Ibid. 57, 7056 (1992).
9. (g) Bridges, R. J.; Stanley, M. S.; Anderson, M. W.; Cotman, C. W.; Chamberlin, R. J. Med. Chem. 34 717 (1991).
10. (h) Humphery, J. M.; Bridges, R. J.; Hart, J. A.; Chamberlin, R. J. Org. Chem. 59, 2467 (1994).
11. (i) Bridges, R. J.; Lovering, F. E.; Humprey, J. M.; Stanley, M. S.; Blakely, T. N.; Cristofaro, M. F.; Chamberlin, A. R. Biorg. Med. Chem. Lett. 3, 115 (1993).
12. (j) Fleet, G. W. Top. Med. Chem. 65 149 (1988).
13. (k) Wang, C. L.; Ripka, W. C.; Confalone, P. N. Tetrahedron Lett. 25, 4613 (1984).
14. () Takano, S.; Samizu, K.; Ogasawara, K. Chem. Lett. 1239 (1990).
15. (m) Goeffrey, N. A.; Baird, P. D.; Fleet, G. W. J.; Peach, J. M.; Smith, P. W.; watkin, D. J. Tetrahedron 43, 3095 (1987).
16. (m) Takano. S.; Moriya, M.; Ogasawara, K. Tetrahedron Asymmetry 3, 681 (1992).
17. For a review of asymmetric 1,3-dipolar cycloaddition reactions see: Gothelf, K. V.; Jorgenson, K. A. Chem. Rev. 98, 863-909 (1998).
18. (a) Garner, P.; Ho, W. B.; Grandhee, S. K.; Youngs, W. J.; Kennedy, V. O. J. Org. Chem. 56, 5893 (1991).
19. (b) Barr, D. A.; Dorrity, M. J.; Grigg, R.; Malone, J. F.; Montgomery, J.; Rajviroongit, S.; Stevenson, P. Tetrahedron Lett. 31, 6569 (1990).
20. Kanemasa, S.; Yamamoto, H. Ibid. 31, 3633 (1990).
21. Kanemasa, S.; Hayashi, T.; Tanaka, J.; Yamamoto, H.; Sakurai, T. J. Org. Chem. 56, 4473 (1991).
22. (e) Fray, A. H.; Meyers, A. I. ibid. 57, 3575 (1992).
23. (f) Waldmann, H.; Blaser, E.; Jansen, M.; Letschert, H.-P. Angew. Chem. Int. ed. 33, 683 (1994).
24. (a) Garner, P. Doǧan, Ö. J. Org. Chem. 59, 4 (1994).
25. (b) Deprez, P.; Royer, J.; Husson, H. P. Tetrahedron Asymmetry 2, 1189 (1991).
26. (c) Williams, R. M.; Zhai, W.; Aidons, D. J.; Aldous, S. C. J. Org. Chem. 57, 6527, (1992).
27. (d) Anslow, A. S.; Harwood, L. M.; Phillips, H.; Watkin, D.; Wong, L. F. Tetrahedron Asymmetry 2, 1343 (1991).
28. (e) Harwood, L. M.; Lilley, I. A. Tetrahedron Lett. 34, 537 (1993).
29. (f) Harwood, L. M.; Manage, A. C.; Robin, S., Hopes, S. F. G.; Watkin, D. J.; Williams, C. E. Synlett 777 (1993).
30. (g) Padwa, A.; Chen, Y. -Y.; Chiacchio, U.; Denat, W. Tetrahedron 41, 3529 (1985).
31. (h) Negron, G.; Roussi, G.; Zhang, J. Heterocylec 34, 293 (1992).
32. Takano, S.; Moriya, M.; Ogasawara, K. Tetrahedron Asymmetry 3, 681 (1992).
33. (j) Bar, D. A.; Dorrity, M. J.; Grigg, R.; Hargreaves, S.; Malone, J. F.; Montgomery, J.; Redpath, J.; Stevenson, P.; Thornton-Pett, M. Tetrahedron 51, 273 (1995).
34. For a review of the use of Oppolzer's sultam, see: Kirn, B. H.; Curran, D. P. Tetrahedron 49, 293 (1993).
35. Garner, P.; Dogan, O.; Pillai, S. Tetrahedron Lett. 35, 1653-1656 (1994).
36. (a) Garner, P., Cox P. B.; Anderson, J. T.; Protasiewicz, J.; Zaniewski, R. J. Org. Chem. 62, 493, (1997).
37. (b) Harwood, L. M.; Lilley, I. A. Tetrahedron Lett. 34, 537, (1993).
38. Takano, S.; Samizu, K.; Ogasawara, K. Chem. Lett. 1239 (1990).
39. (d) Hashimura, K.; Tomita, S.; Hiroya, K.; Ogasawara, K. J. Chem. Soc. Chem. Commun. 2291, (1995). Also, see reference 3.
40. Mungall, W. S.; Greene, G. L.; Heavner, G. A.; Letsinger, R. L. J. Org. Chem. 40, 1659, (1975).
41. Oppolzer, W.; Moretti, R.; Thomi, S. Tetrahedron Lett. 30, 6009, (1989).
42. Urbach, H.; Henning, R. Heterocycles 28, 957, (1989).
43. (a) Huisgen, R.; Scheer, W.; Huber, H. J. Am. Chem. Soc. 89, 1753 (1967).
44. (b) Huisgen, R.; Scheer, W.; Mader, M. Angew. Chem. Int. Ed. 8, 602 and 604, (1969).
45. Hall, J. H.; Huisgen, R. J. Chem. Soc., Chem. Commun. 1187 (1971).
46. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 43, 2923, (1978).