Rapid and efficient chemoselective and multiple sulfations of phenols using sulfuryl imidazolium salts

Tetrahedron Letters

Volumn 52, Issue 26, 2011, Pages 3353-3357

  Taylor, Scott D ^a   Desoky, Ahmed ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

1,8 Diazabicyclo 5.4.0 undec 7 ene; Protecting group; Selectivity; Sulfation; Sulfuryl imidazolium salts

Indexed keywords

ALIPHATIC COMPOUND; HYDROXYL GROUP; IMIDAZOLE DERIVATIVE; PHENOL DERIVATIVE; REAGENT; SULFURYL IMIDAZOLIUM SALT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; CONCENTRATION (PARAMETERS); LOW TEMPERATURE; SULFATION; SYNTHESIS;

EID: 79957581661     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.04.080     Document Type: Article

References (31)

1. J. Kovensky Curr. Med. Chem. 16 2009 2338
2. F.C. Schroeder, A.E. Taggi, M. Gronquist, R.U. Malik, J.B. Grant, T. Eisner, and J. Meinwald Proc. Natl. Acad. Sci. U.S.A. 105 2008 14283
3. L. Kaysser, K. Eitel, T. Tanino, S. Siebenberg, A. Matsuda, S. Ichikawa, and B. Gust J. Biol. Chem. 285 2010 12684
4. M.V. D'Auria, L. Minale, and R. Raffaele Riccio Chem. Rev. 93 1993 1839
5. T.R. Hoye, V. Dvornikovs, J.M. Fine, K.R. Anderson, C.S. Jeffrey, D.C. Muddiman, F. Shao, P.W. Sorensen, and J. Wang J. Org. Chem. 72 2007 7544
6. C. Seibert, and T.P. Sakmar Pept. Sci. 90 2008 459
7. M. Tomishima, H. Ohki, A. Yamada, K. Makib, and F. Ikeda Bioorg. Med. Chem. Lett. 18 2008 2886
8. M.J. Zamek-Gliszczynski, K.A. Hoffmaster, K. Nezasa, M.N. Tallman, and K.L. Brouwer Eur. J. Pharm. Sci. 27 2006 447 486
9. U.R. Desai Med. Res. Rev. 24 2004 151
10. R.A. Al Horani, and U.R. Desai Tetrahedron 66 2010 2907
11. Y. Liu, I.F.F. Lien, S. Ruttgaizer, P. Dove, and S.D. Taylor Org. Lett. 6 2004 209
12. T. Fukuda, T. Ohta, S. Saeki, and M. Iwao Heterocycles 80 2010 841
13. A. Bunschoten, J.A.W. Kruijtzer, J.H. Ippel, C.J.C. de Haas, J.A.G. van Strijp, J. Kemmink, and R.M.J. Liskamp Chem. Commun. 2009 2999
14. Li, X. S.; Robertson, L. W.; Wehmler, H. J. Chem. Cent. J. 2009, 3. doi:10.1186/1752-153X-3-5.
15. A.M. Ali, B. Hill, and S.D. Taylor J. Org. Chem. 74 2009 3583
16. J. Chen, and B. Yu Tetrahedron Lett. 49 2008 1682
17. C.P. Lu, C.T. Ren, S.H. Wu, C.Y. Chu, and L.C. Lo ChemBioChem 8 2007 2187
18. A. Furstner, M.M. Domostoj, and B. Scheiper J. Am. Chem. Soc. 128 2006 8087
19. T. Yamaguichi, T. Fukada, F. Ishibashi, and M. Iwao Tetrahedron Lett. 47 2006 3755
20. A. Furstner, M.M. Domostoj, and B. Scheiper J. Am. Chem. Soc. 127 2005 11620
21. V. Ahmed, M. Ispahany, S. Ruttgaizer, G. Guillemette, and S.D. Taylor Anal. Biochem. 340 2005 80
22. G.T. Gunnarsson, M. Riaz, J. Adams, and U.R. Desai Bioorg. Med. Chem. 13 2005 1783
23. L.J. Ingram, and S.D. Taylor Angew. Chem., Int. Ed. 2006 3503
24. L.J. Ingram, A. Desoky, A.M. Ali, and S.D. Taylor J. Org. Chem. 74 2009 6479
25. A. Desoky, and S.D. Taylor Tetrahedron 67 2011 1281
26. A.D. Proud, J.C. Prodger, and S.L. Flitsch Tetrahedron Lett. 41 1997 7243
27. N.A. Karst, T.F. Islam, F.Y. Avci, and R.J. Lindhardt Tetrahedron Lett. 45 2004 6433
28. +): 482.0488, found 482.0491.
29. A. Raghuraman, M. Riaz, M. Hindle, and U.R. Desai Tetrahedron Lett. 48 2007 6754
30. V.B. Krylov, N.E. Ustyuzhanina, A.A. Grachev, and N.E. Nifantiev Tetrahedron Lett. 49 2008 5877
31. 5 (M+H): 1352.406, found 1352.387.