Synthesis of tetrasubstituted ethylenes on solid support via resin capture

Journal of the American Chemical Society

Volumn 118, Issue 26, 1996, Pages 6331-6332

  Brown, S David ^a   Armstrong, Robert W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030062225     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961203j     Document Type: Article

References (28)

1. (a) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon. E. M. J. Med. Chem. 1994, 37, 1233-1251.
2. (b) Gordon, E. M.; Barrett, R. W.; Dower, W. J., Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385-1401.
3. (a) Bunin, B. A.; Ellman, J. A. J. Am. Chem. Soc: 1992, 114, 10997.
4. (b) Zuckermann, R. N.; Martin, E. J.; Spellmeyer, D. C.; Stauber, G. B.; Shoemaker, K. R.; Kerr, J. M.; Figliozzi, G. M.; Goff, D. A.; Siani, M. A.; Simon, R. J.; Banville, S. C.; Brown, E. G.; Wang, L.; Richter, L. S.; Moos, W. H. J. Med. Chem. 1994, 37, 2678.
5. (c) Murphy, M. M.; Schullek, J. R.; Gordon, E. M.; Gallop, M. A. J. Am. Chem. Soc. 1995, 117, 7029.
6. (d) Tempest, P. A.; Brown, S. D.; Armstrong, R. W. Angew. Chem., Int. Ed. Engl. 1996, 35, 640.
7. (e) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123.
8. Cheng, S.; Comer, D. D.; Williams, J. P.; Myers, P. L.; Boger, D. L. J. Am. Chem. Soc. 1996, 118, 2567.
9. Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 2574.
10. For a review, see: van den Koedijk, C. D.; Blankenstein, M. A.; Thijssen, J. H. Biochem. Pharmacol. 1994, 47, 1927.
11. Harper, M. J. K.; Walpole, A. L. Nature (London) 1966, 212, 87.
12. For the latest research, see: (a) Callaghan, R.; Higgins, C. F. Brit. J. Cancer 1995, 71, 294. (b) Kirk, J.; Syed, S. K.; Harris, A. L.; Jarman, M.; Roufogalis, B. D.; Stratford, I. J.; Carmichael, J. Biochem. Pharmacol. 1994, 48, 277. (c) Nephew, K. P.; Polek, T. C.; Khan, S. A. Endocrinology 1996, 137, 219.
13. For the latest research, see: (a) Callaghan, R.; Higgins, C. F. Brit. J. Cancer 1995, 71, 294. (b) Kirk, J.; Syed, S. K.; Harris, A. L.; Jarman, M.; Roufogalis, B. D.; Stratford, I. J.; Carmichael, J. Biochem. Pharmacol. 1994, 48, 277. (c) Nephew, K. P.; Polek, T. C.; Khan, S. A. Endocrinology 1996, 137, 219.
14. For the latest research, see: (a) Callaghan, R.; Higgins, C. F. Brit. J. Cancer 1995, 71, 294. (b) Kirk, J.; Syed, S. K.; Harris, A. L.; Jarman, M.; Roufogalis, B. D.; Stratford, I. J.; Carmichael, J. Biochem. Pharmacol. 1994, 48, 277. (c) Nephew, K. P.; Polek, T. C.; Khan, S. A. Endocrinology 1996, 137, 219.
15. (a) Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018.
16. (b) Ishiyama, T.; Matsuda, N.; Murata, M.; Ozawa, F.; Suzuki, A.; Miyaura, N. Organometallics 1996, 15, 713.
17. (a) Backes, B. J.; Ellman, J. A. J. Am Chem. Soc. 1994, 116, 11171.
18. (b) Frenette, R.; Friesen, R. W. Tetrahedron Lett. 1994, 35, 9177.
19. (c) Boojamra, C. G.; Burow, K. M.; Ellman, J. A. J. Org. Chem. 1995, 60, 5742.
20. (d) Goff, D. A.; Zuckermann, R. N. J. Org Chem. 1995, 60, 5744.
21. Johnson, S. G. Presented at the 211th National Meeting of the American Chemical Society, New Orleans, LA, March 1996; paper ORGN 126.
22. 2.
23. 2.
24. The opposite order of addition of halides produced resin-bound boronate 7 very efficiently. However, subsequent condensation with solution aryl halides occurred in unacceptable yields. equal presented
25. 11b is the result of hydrolytic deboration of 7 during the Suzuki reaction (see ref 13). Resin capture minimizes the amount of deborated material that collects on the polymer since it avoids resin-bound vinyl boronates like 7. equal presented
26. Richter, L. S.; Gadek, T. R. Tetrahedron Lett. 1994, 35, 4705.
27. Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508.
28. This material is the result of unreacted 2 coupling to the resin followed by deboration of the intermediate 7 (see ref 14).