Simple and efficient method for the oxidation of sulfides to sulfoxides: Application to the preparation of glycosyl sulfoxides

Journal of Organic Chemistry

Volumn 61, Issue 23, 1996, Pages 8347-8349

  Kakarla, Ramesh ^a   Dulina, Richard G ^a   Hatzenbuhler, Nicole T ^a   Hui, Y W ^a   Sofia, Michael J ^a  

^a Transcell Technologies Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE; SULFOXIDE;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY;

EID: 0029849815     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961478h     Document Type: Article

References (43)

1. (a) Field, L. Synthesis 1978, 713.
2. (b) Block, E. Reactions of Organosulfur Compounds; Academic: New York, 1978.
3. (c) Durst, T. in Comprehensive Organic Chemistry; Barton, D., Ollis, W. D., Eds.; Pergman: Oxford, U.K., 1979; Vol. 3.
4. (d) Solladie, G. Synthesis 1981, 185.
5. (e) Ikemoto, N.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 9657.
6. (f) Stork, G.; Kim, G. J. Am. Chem. Soc. 1992, 114, 1087.
7. (g) Berkowitz, D. B.; Schulte, G. K; Danishefsky, S. J. Am. Chem. Soc. 1992, 114, 4518.
8. (h) Moghaddam, F. M.; Ghaffarzadeh, M. Tetrahedron Lett. 1996, 37, 1855.
9. Kahne, D.; Walker, S.; Cheng, Y.; Van Engen, D. J. Am. Chem. Soc. 1989, 111, 6881.
10. Sliedregt, L. A.; Van Der Marel, G. A.; Van Boom, J. H. Tetrahedron Lett. 1994, 35, 4015.
11. (b) Alonso, I.; Khiar, N.; Martin-Lomas, M. Tetrahedron Lett. 1998, 37, 1477.
12. (a) Voelter, W.; Wang, Y.; Zhang, H. Tetrahedron Lett. 1995, 36, 1234;
13. (b)Z. Naturforsch. 1995, 50b, 661.
14. (c) Khiar, N.; Martin-Lomas, M. J. Org. Chem. 1995, 60, 7017.
15. (a) Yang, D.; Kirn, S.-H.; Kahne, D. J. Am. Chem. Soc. 1991, 113, 4715.
16. (b) Cheng, Y.; Ho, D. M.; Gottlieb, C. R; Kahne, D.; Bruck, M. A. J. Am. Chem. Soc. 1992, 114, 7319.
17. (c) Kahne, D.; Raghavan, S. J. Am. Chem. Soc. 1993, 115, 1580.
18. (d) Kim, S.-H.; Augeri, D.; Yang, D.; Kahne, D. J. Am. Chem. Soc. 1994, 116, 1766.
19. Yan, L.; Taylor, C. M.; Goodnow, R.; Kahne, D. J. Am. Chem. Soc. 1994, 116, 6953.
20. Walker, S. Ph.D. Dissertation, Princeton University, 1991.
21. (a) Walker, S.; Sofia, M. J.; Kakarla, R.; Kogan, N. A.; Wierichs, L.; Longley, C. B.; Brucker, K.; Axelrod, H. R.; Midha, S.; Babu, S.; Kahne, D. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 1585.
22. (b) Longely, C. B.; Axelrod, H. R.; Midha, S.; Kakarla, R.; Kogan, N. A.; Sofia, M. J.; Babu, S.; Wierichs, L.; Walker, S. Ann. N.Y. Acad. Sci. U.S.A. 1995, 772, 268.
23. (c) Kakarla, R.; Kogan, N. A.; Dulina, R. G; Hui, Y. W., Hatzenbuhler, N. T.; Liu, D.; Chen, A.; Wagler, T.; Sofia, M. J. 211th ACS National Meeting, New Orleans, 1996; Abstract No. 320 (Div. of Org. Chem.).
24. (a) Patai, S., Rappoport, Z., Eds, The Chemistry of Sulphones, Sulphoxides and Cyclic Sulphides; John Wiley and Sons: Chichester, U.K., 1994.
25. (b) Uemura, S. In Comprehensive Organic Synthesis; Ley, S. V., Ed.; Pergman: Oxford, 1991; Vol. 7, p 757.
26. (c) Fabretti, A.; Ghelfi, F.; Grandi, R.; Pagnoni, U. M. Synth. Commun. 1994, 24, 2393.
27. (d) Siedlecka, R.; Skarzewski, J. Synthesis 1994, 401.
28. (e) Desmartean, D. D.; Petrov, V. A.; Montanari, V.; Pregnolato, M.; Resnati, G. J. Org. Chem. 1994, 59, 2762.
29. (f) Adam, W.; Mitchell, C. M.; Saha-Moller, C. R. Tetrahedron 1994, 50, 13121.
30. (g) Breton, G. W.; Fields, J. D.; Kropp, P. J. Tetrahedron Lett. 1995, 36, 3825.
31. (h) Onto, K.; Hatakeyama, T.; Takeo, M.; Suginome, H. Synthesis 1995, 1357.
32. (i) Aldea, R.; Alper, H. J. Org. Chem. 1995, 60, 8365.
33. (j) Procter, D. J.; Thornton-Pett, M.; Rayner, C. M. Tetrahedron Lett. 1996, 37, 1841.
34. (k) Arterburn, J. B.; Nelson, S. L. J. Org. Chem. 1996, 61, 2260.
35. (l) Khanna, V.; Maikap, G. C.; Iqbal, J. Tetrahedron Lett. 1996, 37, 3367.
36. Schmidt, R. R.; Kast, J. Tetrahedron Lett. 1986, 27, 4007.
37. Balicki, R.; Kaczmarek, L.; Nantki-Namirski, P. Liebigs Ann. Chem. 1992, 883.
38. (a) Ferner, R. J.; Furaneaux, R. H. Methods Carbohydr. Chem. 1980, 8, 251.
39. (b) Ferner, R. J.; Hay, R. W.; Vethaviyasar, N. Carbohydr. Res. 1973, 27, 55.
40. (c) Akiya, Y.; Osawa, T. Yakugaku Zasshi 1957, 77, 726.
41. (d) Vasella, A.; Witzig, C.; Chiara, J.-L.; Martin-Lomas, M. Helv. Chim. Acta 1991, 74, 2073.
42. (e) Albert, R.; Dax, K.; Pleschko, R.; Stutz, A. Carbohydr. Res. 1985, 137, 282.
43. Orito, K.; hatakeyama, T.; Takeo, M.; Suginome, H. Synthesis 1995, 1357.