Efficient synthesis of sulfonic, phosphoric, and phosphinic esters employing alkylating polymer-bound reagents

Journal of Combinatorial Chemistry

Volumn 5, Issue 2, 2003, Pages 138-144

  Vignola, Nicola ^a   Dahmen, Stefan ^a   Enders, Dieter ^a   Bräse, Stefan ^b  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b UNIVERSITY OF BONN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATING AGENT; PHOSPHINIC ACID DERIVATIVE; PHOSPHORIC ACID DERIVATIVE; POLYMER; SULFONIC ACID DERIVATIVE; TRIAZENE DERIVATIVE;

ARTICLE; CHEMICAL BOND; ESTERIFICATION; PURIFICATION; SYNTHESIS;

EID: 0141687204     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc0200787     Document Type: Article

References (56)

1. Kalir, A.; Kalir, H. H. In The chemistry of sulphonic acids esters and their derivatives; Patai, S., Rappoport. Z., Eds.; John Wiley: New York, 1991; pp 767-788.
2. Crossland, R. K.; Wells, W. E.; Shiner, Jr, V. J. J. Am. Chem. Soc. 1971, 93, 4217-4219.
3. (a) Ninomiya, S.; Kohda, K.; Kawazoe, Y. Chem. Pharm. Bull 1984, 32, 1326-1332.
4. (b) Hakura, A.; Ninomiya, S.; Kohda, K.; Kawazoe, Y. Chem. Pharm. Bull. 1984, 32, 3626-3635.
5. (c) Miller, J. A. Cancer Res. 1970, 30, 559-576.
6. (d) Peterson, A. R.; Landolph, J. R.; Peterson, H.; Spears, C. P.; Heidelberger, C. Cancer Res. 1981, 41, 3095-3099.
7. Marques, V. E.; Sharma, R.; Wang, S.; Lewin, N. E.; Blumberg, P. M.; Kim, I.; Lee, J. Bioorg. Med. Chem. Lett. 1998, 8, 1757-1762.
8. Zhong, Z.; Bibbs, J. A.; Yuan, W.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 2259-2263.
9. Philipp, M.; Bender, M. L. Mol. Cell. Biochem. 1983, 51, 5-32.
10. Shealy, Y. F.; Krauth, C. A.; Struck, R. F.; Montgomery, J. A. J. Med. Chem. 1983, 26, 1168-1173.
11. Shealy, Y. F.; Krauth, C. A. J. Pharm. Sci. 1993, 82, 1200.
12. Huang, J.; Widlanski, T. S. Tetrahedron Lett. 1992, 33, 2657-2660.
13. Hoyle, J. In The chemistry of sulphonic acids esters and their derivatives; Patai, S., Rappoport Z., Eds.; John Wiley: New York, 1991; pp 351-400.
14. Choe, Y. S.; Katzenellenbogen, J. A. Tetrahedron Lett. 1993, 34, 1579-1580.
15. King, J. F. Acc. Chem. Res. 1975, 8, 10-17.
16. King, J. F.; Lam, J. Y. L.; Skonieczny, S. J. Am. Chem. Soc. 1992, 114, 1743-1749.
17. Trujillo, J. I.; Gopalan, A. S. Tetrahedron Lett. 1993, 34, 7355-7358.
18. Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5335-5340.
19. Voronkov, M. G.; Knutov, V. I.; Shevko, O. N. Chem. Heterocycl. Compd. 1992, 28, 586-599.
20. (a) Windaus, A.; Kuhr, E. Liebigs Ann. Chem. 1937, 532, 52-68.
21. (b) Treibs, W.; Lorenz, I. Chem. Ber. 1949, 82, 400-405.
22. (c) Geiseler, G.; Kuschmiers, R. Chem. Ber. 1958, 91, 1881-1891.
23. (d) Hansen, H. C.; Kice, J. L. J. Org. Chem. 1983, 48, 2943-2949.
24. (e) Corey, E. J.; Cimprich, K. A. Tetrahedron Lett. 1992, 33, 4099-4102.
25. (f) Ishiyama, H.; Ishibashi, M.; Ogawa, A.; Yoshida, S.; Kobayashi, J. J. Org. Chem. 1997, 62, 3831-3836.
26. (a) Meese, C. O. Synthesis 1984, 1041-1042.
27. (b) Reichstein, T.; Schindler, W. Helv. Chim. Acta 1940, 23, 669-675.
28. (c) Scott, R. B.; Lutz, R. E. J. Org. Chem. 1954, 19, 830-839.
29. Zollinger, H. Diazo Chemistry; VCH: Weinheim, 1994.
30. Technical Bulletin AL-180 (Aldrich).
31. Bräse, S.; Köbberling, J.; Enders, D.; Wang, M.; Lazny, R.; Brandtner, S. Tetrahedron Lett. 1999, 40, 2105-2108.
32. Dahmen, S.; Bräse, S. Org. Lett. 2000, 2, 3563-3565.
33. Bräse, S.; Dahmen, S.; Pfefferkorn, M. J. Comb. Chem. 2000, 2, 710-717.
34. (a) Pilot, C. Matrise de Chimie, RWTH Aachen 1999.
35. (b) Bräse, S. Chim. Oggi 2000, 18, 14-19.
36. (c) Bräse, S.; Dahmen, S. Chem. Eur. J. 2000, 6, 1899-1905.
37. (d) Pilot, C.; Dahmen, S.; Lauterwasser, F.; Bräse, S. Tetrahedron Lett. 2001, 42, 9179-9181.
38. (a) Rademann, J.; Smerdka, J.; Jung, G.; Grosche, P.; Schmid, D. Angew. Chem. 2001, 113, 390-394; Angew. Chem. Int. Ed. 2001, 40, 381-385.
39. (a) Rademann, J.; Smerdka, J.; Jung, G.; Grosche, P.; Schmid, D. Angew. Chem. 2001, 113, 390-394; Angew. Chem. Int. Ed. 2001, 40, 381-385.
40. (b) For a review about polymer-bound reagents, see: Handbook of Combinatorial Chemistry, Drugs, Catalysts, Materials: Nicolaou, K. C., Hanko, R., Hartwig, W., Eds.; Wiley-VCH: Weinheim, 2002.
41. Vignola, N.; Dahmen, S.; Enders, D.; Bräse, S. Tetrahedron Lett. 2001, 42, 7833-7836.
42. Dahmen, S.; Bräse, S. Angew. Chem. 2000, 112, 3827-3830; Angew. Chem. Int. Ed. 2000, 39, 3681-3684.
43. Dahmen, S.; Bräse, S. Angew. Chem. 2000, 112, 3827-3830; Angew. Chem. Int. Ed. 2000, 39, 3681-3684.
44. Enders, D.; Vignola, N.; Berner, O. M.; Bats, J. W. Angew. Chem. 2002, 114, 116-119; Angew. Chem. Int. Ed. 2002, 41, 109-111.
45. Enders, D.; Vignola, N.; Berner, O. M.; Bats, J. W. Angew. Chem. 2002, 114, 116-119; Angew. Chem. Int. Ed. 2002, 41, 109-111.
46. (a) Kolovos, M.; Froussios, C. Tetrahedron Lett. 1984, 25, 3909-3912.
47. (b) Ali, S.; Bittman, R. J. Org. Chem. 1988, 53, 5547-5549.
48. (c) Yuasa, H.; Hindsgaul, O.; Palcic, M. M. J. Am. Chem. Soc. 1992, 114, 5891-5892.
49. (d) Badet, B.; Julia, M.; Rolando, C. Synthesis 1982, 291-294.
50. (a) Emmick, T. L.; Letsinger, R. L. J. Am. Chem. Soc. 1968, 90, 3459-3465.
51. (b) Renard, P.-Y.; Vayron, P.; Taran, F.; Mioskowski, C. Tetrahedron Lett. 1999, 40, 281-284.
52. Choudary, B. M.; Chowdari, N. S.; Kantam, M. L. Tetrahedron 2000, 56, 7291-7298.
53. Patterson, T. S.; Loudon, J. D. J. Chem. Soc 1932, 1725-1744.
54. Huang, T. S. C. C.; Thornton, E. R. J. Am. Chem. Soc. 1976, 98, 1542-1545.
55. Truce, W. E.; Campbell, R. W.; Madding, G. D. J. Org. Chem. 1967, 32, 308-317.
56. The analytical data of this compound will be published elsewhere.