Observations on the reactivity of pentafluorophenyl sulfonate esters

Chemical Communications

Volumn , Issue 21, 2005, Pages 2727-2728

  Caddick, Stephen ^a   Wilden, Jonathan D ^a   Judd, Duncan B ^b  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; ESTER DERIVATIVE; PENTAFLUOROPHENYLSULFONATE ESTER DERIVATIVE; SULFONAMIDE; SULFONIC ACID DERIVATIVE; SULFONYL CHLORIDE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPARATIVE STUDY; ELIMINATION REACTION; REACTION ANALYSIS;

EID: 20744432901     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b501212k     Document Type: Article

References (17)

1. (a) T. H. Maren, Ann. Rev. Pharmacol. Toxicol., 1976, 16, 309;
2. (b) C. T. Suparan, F. Brigand, S. Tilli, W. R. Chegwidden and A. Scozzafaza, Bioorg. Med. Chem., 2001, 9, 703.
3. (a) W. R. Roush, S. L. Gwaltney, II, J. M. Cheng, K. A. Scheidt, J. H. McKerrow and E. Hansell, J. Am. Chem. Soc., 1998, 120, 10994;
4. (b) J. J. Reddick, J. M. Cheng and W. R. Roush, Org. Lett., 2003, 5, 1967;
5. (c) A. A. Hernandez and W. R. Roush, Curr. Opin. Chem. Biol, 2002, 6, 459;
6. (d) W. R. Roush, J. M. Cheng, B. Knapp-Reed, A. Alvarez-Hernandez, J. H. McKerrow, E. Hansell and J. C. Engel, Bioorg. Med Chem. Lett., 2001, 11, 2759.
7. S. Caddick, J. D. Wilden, S. J. Wadman, H. D. Bush and D. B. Judd, Org. Lett., 2002, 4, 2549.
8. S. Caddick, J. D. Wilden and D. B. Judd. J. Am. Chem. Soc., 2004, 126, 1024.
9. (a) For a complete overview of this mechanism, see: I. M. Gordon, H. Maskill and M. F. Ruasse, Chem. Soc. Rev., 1989, 18, 123 and references therein;
10. (b) J. F. King, J. Y. L. Lam and S. Skonieczny, J. Am. Chem. Soc., 1992, 114, 1743;
11. (c) S. N. Lyashchuck, Y. G. Skrypnik and V. P. Besrodnyi, J. Chem. Soc., Perkin Trans. 2, 1993, 6, 1153.
12. (a) L. Kisfalud, M. Low, O. Nyeki, T. Szirtes and I. Schon, Liebigs Ann. Chem., 1973, 1421;
13. (b) L. Kisfalud, J. E. Roberts, R. H. Johnson, G. L. Mayers and J. Kovacs, J. Org. Chem., 1970, 35, 3563;
14. (c) B. Penke, L. Balaspiri, P. Pallai and K. Kovacs, Acta Phys. Chem., 1974, 20, 471;
15. (d) L. Kisfalud and I. Schon. Synthesis, 1983, 325.
16. T. Kimura and T. Ando, J. Synth. Org. Chem. Jpn., 1988, 46, 1124.
17. R. Miethchen, Ultrasonics, 1992, 30, 173.