Solid-Phase Preparation of Dienes

Journal of Organic Chemistry

Volumn 63, Issue 4, 1998, Pages 1119-1125

  Blaskovich, Mark A ^a,b   Kahn, Michael ^a,b  

^a Molecumetics Ltd   (United States)

^b UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000744486     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9715884     Document Type: Article

References (48)

1. Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, (a) 1233-1251
2. Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37 (b) 1385-1401.
3. (c) Terrett, N. K.; Gardner, M. G.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135-8173.
4. (d) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-4554.
5. (e) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600.
6. (f) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42.
7. (g) Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288-2337.
8. See entire issue 5 of Biorg. Med. Chem. 1996, 4, 631-737 for recent examples.
9. (a) Yedidia, V.; Leznoff, C. C. Can. J. Chem. 1980, 58, 1144-1150 (acrylic acid on Merrifield resin, react with two dienes and cleave from resin).
10. (b) Keana, J. F. W.; Guzikowski, A. P.; Ward, D. D.; Morat, C.; Van Nice, F. L. J. Org. Chem. 1983, 48, 2654-2660 (urazole on silica, used to remove several dienes from solution, one prodict-ergosterol adduct-cleaved and isolated).Ritter, H.; Sperber, R. Macromolecules 1994, 27, 5919-5920 (alkene in poly(vinylformyl) resin, reacted with heterodiene, no product cleaved).
11. (b) Keana, J. F. W.; Guzikowski, A. P.; Ward, D. D.; Morat, C.; Van Nice, F. L. J. Org. Chem. 1983, 48, 2654-2660 (urazole on silica, used to remove several dienes from solution, one prodict-ergosterol adduct-cleaved and isolated).Ritter, H.; Sperber, R. Macromolecules 1994, 27, 5919-5920 (alkene in poly(vinylformyl) resin, reacted with heterodiene, no product cleaved).
12. (a) Gavina, F.; Palazon, B. Tetrahedron Lett. 1979, 15, 1333-1336 (butadienol attached as ester to polystrylacetyl resin, reacted with diimine, cleaved in 18% yield).
13. (b) Guhr, K. I.; Greaves, M. D.; Rotello, V. M. J. Am. Chem. Soc. 1994, 116, 5997-5998 (cyclopentadiene on Merrifield resin, add buckminsterfullerene, no cleaved product).
14. (c) Sclessinger, R. H.; Bergstrom, C. P. Tetrahedron Lett. 1996, 37, 2133-2136 (furan on silylated polystyrene resin, several dienophiles, product cleaved and isolated).
15. (a) Leznoff, C. C.; Wong, J. Y. Can. J. Chem. 1973, 51, 3756-3764 (1,4-diphenyl Z diene by Wittig reaction).
16. (b) Leznoff, C. C.; Greenberg, S. Can. J. Chem. 1976, 54, 3824-3829 (1,4-diphenyl E diene by Wittig reaction).
17. (c) Nieuwstad, TH. J.; Kieboom, A. P. G.; Beijer, A. J.; Van Der Linden, J.; Van Bekkum, H. Recl. Trav. Chim. Pays-Bas 1976, 95, 225-231 (diene on polymer by desulfuration or by Grignard addition/elimination).
18. (d) Leznoff, C. C.; Sywanyk, W. J. Org. Chem. 1977, 42, 3203-3205 (carotenoid tetra-, hexa-, and heptaenes on polystyrene support).
19. (e) Johnson, C. R.; Zhang, B. Tetrahedron Lett. 1995, 36, 9253-9256 (Wittig-Horner olefination with cinnamaldehyde).
20. (a) Douglas, S. P.; Whitfield, D. M.; Krepinsky, J. J. J. Am. Chem. Soc. 1991, 113, 5095-5097.
21. (b) Han, H.; Wolfe, M. M.; Brenner, S.; Janda, K. D. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 6419-6423.
22. (c) Zhu, J.; Hegedus, L. S. J. Org. Chem. 1995, 60, 5831-5837.
23. (d) Park, W. K. C.; Auer, M.; Jaksche, H.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 10150-10155.
24. (a) Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183-2186.
25. (b) Rathke, M. W.; Nowak, M. J. Org. Chem. 1985, 50, 2624-2626.
26. (a) Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972-980.
27. (b) Uenishi, J.-I.; Beau, J.-M.; Armstrong, R. W.; Kishi, Y. J. Am. Chem. Soc. 1987, 109, 4765-4758.
28. (a) Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1994, 116, 11171-11172.
29. (b) Frenette, R.; Friesen, R. W. Tetrahedron Lett. 1994, 35, 9177-9180.
30. (c) Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169-5171.
31. (d) Koh, J. S.; Ellman, J. A J. Org. Chem. 1996, 61, 4494-4495.
32. (e) Boojamra, C. G.; Burow, K. M.; Ellman, J. A. J. Org. Chem. 1995, 60, 5742-5743.
33. (f) Brown, S. D.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 6331-6332.
34. (g) Han, Y.; Walker, S. D.; Young, R. N. Tetrahedron Lett. 1996, 37, 2703-2706.
35. (h) Chenera, B.; Finkelstein, J. A.; Veber, D. J. Am. Chem. Soc. 1995, 117, 11999-12000.
36. Stille, J. K. Pure Appl. Chem. 1985, 57, 1771-1780.
37. (a) Forman, F. W.; Sucholeiki, I. J. Org. Chem. 1995, 60, 523-528 (tributylphenyltin or iodobenzene attached by amide bond to Rink amide resin, coupled with aryl halides/triflates or trialkylphenyltin, respectively).
38. (b) Beaver, K. A.; Siegmund, A. C.; Spear, K. L. Tetrahedron Lett. 1996, 37, 1145-1148 (iodobenzene attached by sulfonamide linker on Rink resin, coupled with 1-(ethoxyvinyl)-tributyltin).
39. Deshpande, M. S. Tetrahedron Lett. 1994, 35, 5613-5614 (iodobenzoic acid on Rink or Wang resin, coupled with five organostannanes).
40. (a) Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1995, 60, 6006-6007 (aryltrimethyltin on (aminomethyl)polystyrene resin, couple with four acid chlorides).
41. (b) Plunkett, M. J.; Ellman, J. A. J. Am. Chem. Soc. 1995, 117, 3306-3307 (arylstannane on (aminomethyl)polystyrene resin, couple with 15 acid chloride intermediates).
42. (a) Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813-817.
43. (b) Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585-9595.
44. Boden, C. D. J.; Pattenden, G.; Ye, T. J. Chem. Soc., Perkin Trans. 1 1996, 2417-2419.
45. Asao, N.; Liu, J.-X.; Sudoh, T.; Yamamoto, Y. J Org. Chem. 1996, 67, 4568-4571.
46. 3. Only DIC was used for coupling of the bromoacrylic acid to the resin-bound amino acid, as it was found that other coupling reagents (PyBOP) or the presence of base (DIPEA) resulted in impure product.
47. Grout, D. H. G.; Corkill, J. A. Tetrahedron Lett 1977, 49, 4355-4357.
48. Carpino, L. A.; Shroff, H.; Triolo, S. A.; Mansour, E.-S. M. E.; Wenschuh, H.; Albericio, F. Tetrahedron Lett. 1993, 34, 7829-7832.