Acceleration of acid-catalyzed transesterification of 2-hydroxypropyl-p-nitrophenyl phosphate by organic solvents

Organic Letters

Volumn 2, Issue 3, 2000, Pages 377-380

  Hong, In Seok ^a   Suh, Junghun ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000564964     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991321m     Document Type: Article

References (39)

1. Williams, N. H.; Takasaki, B.; Wall, M.; Chin, J. Acc. Chem. Res. 1999, 32, 485.
2. Breslow, R.; Labelle, M. J. Am. Chem. Soc. 1986, 108, 2655.
3. Jubian, V.; Dixon, R. P.; Hamilton, A. D. J. Am. Chem. Soc. 1992, 114, 1120.
4. Barbier, B.; Brack, A. J. Am. Chem. Soc. 1992, 114, 3511.
5. Göbel, M. W.; Bats, J. W.; Dürner, G. Angew. Chem., Int., Ed. Engl. 1992, 31, 207.
6. Smith, J.; Ariga, K.; Anslyn, E. V. J. Am. Chem. Soc. 1993, 115, 362.
7. Breslow, R.; Huang, D. L.; Anslyn, E. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 1746.
8. Stern, M. K.; Bashkin, J. K.; Sall, E. D. J. Am. Chem. Soc. 1990, 112, 5357.
9. Chin, J. Acc. Chem. Res. 1991, 25, 145.
10. Vance, D. H.; Czarnik, A. W. J. Am. Chem. Soc. 1993, 115, 12165.
11. Wall, M.; Hynes, R. C.; Chin, J. Angew. Chem., Int., Ed. Engl. 1993, 32, 1633.
12. Bashkin, J. K.; Frolova, E. I.; Sampath, U. J. Am. Chem. Soc. 1994, 116, 5981.
13. Chapman, W. H., Jr.; Breslow, R. J. Am. Chem. Soc. 1995, 117, 5462.
14. Young, M. J.; Chin, J. J. Am. Chem. Soc. 1995, 117, 10577.
15. Linkletter, B.; Chin, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 472.
16. Wahnon, D.; Lebuis, A.-M.; Chin, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2412.
17. Koike, T.; Inoue, M.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1996, 118, 3091.
18. Ragunathan, K. G.; Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1219.
19. Williams, N. H.; Chin, J. J. Chem. Soc., Chem. Commun. 1996, 131.
20. Molenveld, P.; Kapsabelis, S.; Engberson, J. F. J.; Reinhoudt, D. N. J. Am. Chem. Soc. 1997, 119, 2948.
21. Hettich, R.; Schneider, H.-J. J. Am. Chem. Soc. 1997, 119, 5638.
22. Liu, S.; Hamilton, A. D. Tetrahedron Lett. 1997, 38, 1107.
23. Liu, S.; Hamilton, A. D. Bioorg. Med. Chem. Lett. 1997, 7, 1779.
24. Molenveld, P.; Engberson, J. F. J.; Kooijman, H.; Speck, A. L.; Reinhoudt, D. N. J. Am. Chem. Soc. 1998, 120, 6726.
25. Suh, J.; Hong, S. H. J. Am. Chem. Soc. 1998, 120, 12545.
26. Morrow, J. R.; Buttrey, L. A.; Shelton, V. M.; Berback, K. A. J. Am. Chem. Soc. 1992, 114, 1903.
27. Schneider, H.-J.; Rammo, J.; Hettich, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1716.
28. Kalesse, M.; Loos, A. Bioorg. Med. Chem. Lett. 1996, 6, 2063.
29. Perrault, D. M.; Anslyn, E. V. Angew. Chem., Intl. Ed. Engl. 1997, 36, 432.
30. For structures and mechanisms of phosphoester hydrolases, see: Hannon, C. L.; Anslyn, E. V. In Bioorganic Chemistry Frontiers; Dugas, H., Ed.; Springer-Verlag: Berlin, 1993; Vol. 3, pp 193-255.
31. Chin, J.; Banaszczyk, M.; Jubian, V.; Zou, X. J. Am. Chem. Soc. 1989, 111, 186.
32. Bryant, R. A. R.; Hansen, D. E. J. Am. Chem. Soc. 1996, 118, 5498.
33. Radzicka, A.; Wolfenden, R. J. Am. Chem. Soc. 1996, 118, 6105.
34. Smith, R. M.; Hansen, D. E. J. Am. Chem. Soc. 1998, 120, 8910.
35. 3CN, respectively, identical chemical shifts (0.55 ppm) were obtained for the phosphorus atom of the product. In the same solvent, chemical shift for HPNPP was -5.2 ppm.
36. 4 is fully ionized: Kolthoff, I. M.; Bruckenstein, S.; Chantooni, M. K. Jr. J. Am. Chem. Soc. 1961, 83, 3927.
37. Jencks, W. P.; Regenstein, J. In Handbook of Biochemistry and Molecular Biology, 3rd ed.; Fasman, G. D., Ed.; CRC Press: Cleveland, 1976; Vol. 1, pp 305-351.
38. Isaacs, N. S. Physical Organic Chemistry, 2nd ed.; Longman: Burnt Mill, 1995; Chapter 5.
39. The degree of acceleration of HPNPP transesterification in the presence of bis(guanidinium) receptors was higher in acetonitrile than in water (Oost, T.; Filippazzi, A.; Kalesse, M. Liebigs Ann. 1997, 1005). In this case, strengthening the hydrogen bonding between HPNPP and the host by the organic solvent would make a major contribution to the observed solvent effect.