Development of a novel silyl ether linker for solid-phase organic synthesis

Journal of Organic Chemistry

Volumn 61, Issue 19, 1996, Pages 6498-6499

  Boehm, Terri L ^a   Showalter, H D Hollis ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000576958     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961242d     Document Type: Article

References (21)

1. A preliminary account of this work was presented at the 211th American Chemical Society National Meeting, New Orleans, LA, March 1996; Abstract BIOT 0121.
2. Merrifield, R. B. Chem. Scr. 1985, 25, 121-141. Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149-2154.
3. Merrifield, R. B. Chem. Scr. 1985, 25, 121-141. Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149-2154.
4. Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385-1401.
5. Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600.
6. Sucholeiki, I. Tetrahedron Lett. 1994, 35, 7307.
7. (a) Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1995, 60, 6006-6007.
8. (b) Chenera, B.; Finkelstein, J. A.; Veber, D. F. J. Am. Chem. Soc. 1995, 117, 11999-12000.
9. (c) Han, Y.; Walker, S. D.; Young, R. N. Tetrahedron Lett. 1996, 37, 2703-2706.
10. Protecting Groups in Organic Synthesis, 2nd ed.; Greene, T. W., Wuts, P. G. M., Eds.; Wiley: New York, 1991.
11. Randolph, J. T.; McClure, K. F.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5712-5719.
12. For an example, see; Mullen, D. G.; Barany, G. J. Org. Chem. 1988, 53, 5240-5248.
13. (a) Cagniant, P.; Cagniant, D. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic: New York, 1975; Vol. 18, pp 337-482.
14. (b) Mustafa, A. In Chemistry of Heterocyclic Compounds; Weissberger, A., Taylor, E. C., Eds.; Wiley: New York, 1974; Vol. 29, pp 1-514.
15. Hatanaka, Y.; Yoshida, E.; Nakayama, H.; Kanaoka, Y. Bioorg. Chem. 1989, 17, 482-485.
16. Harvey, R. G.; Hahn, J.-T.; Bukowska, M.; Jackson, H. J. Org. Chem. 1990, 55, 6161-6166.
17. Frigerio, M.; Santagostino, M.; Sputore, S.; Palmisano, G. J. Org. Chem. 1995, 60, 7272-7276.
18. Funk, R. L.; Vollhart, K. P. C. J. Am. Chem. Soc. 1980, 102, 5253-5261.
19. Stork, G.; Chan, T. Y.; Breault, G. J. Am. Chem. Soc. 1992, 114, 7578-7579.
20. The substitution level was determined by treating the solid support with TBAF in THF at room temperature for 24 h, which resulted in cleavage of the silicon-oxygen bond. On the basis of the mass of the recovered silanol 3, the resin loading was determined to be 0.72 mmol/g.
21. 2 at 0 °C provided a 76% yield of a 1:1 mixture of the desired compound, 1-[5-bromo-3-(4-methoxyphenyl)benzofuran-2-yl]-2,2-dimethylpropan-1-one, as well as 1-[5-bromo-3-(3-bromo-4-methoxyphenyl)benzofuran-2-yll-2,2-dimethylpropan-1-one resulting from a second bromination of the 3-aryl substituent.