Osmium catalyzed dihydroxylation of 1,2-dioxines: A new entry for stereoselective sugar synthesis

Journal of Organic Chemistry

Volumn 71, Issue 19, 2006, Pages 7236-7244

  Robinson, Tony V ^a   Taylor, Dennis K ^a   Tiekink, Edward R T ^b  

^a UNIVERSITY OF ADELAIDE   (Australia)

^b UNIVERSITY OF TEXAS AT SAN ANTONIO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; DERIVATIVES; HYDROXYLATION; NITROGEN COMPOUNDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ACETONIDE; DIHYDROXYLATION; HYDROXY KETONES; OSMIUM TETROXIDE;

SUGARS;

1,2 DIOXINE DERIVATIVE; 3,6 DIHYDRO 1,2 DIOXINE DERIVATIVE; ACETONIDE DERIVATIVE; ALCOHOL DERIVATIVE; CARBOHYDRATE; COBALT COMPLEX; KETOL; KETONE; OSMIUM; OSMIUM TETRAOXIDE; OXYGEN DERIVATIVE; PEROXY DIOL DERIVATIVE; PSICOSE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; CATALYSIS; CATALYST; DIHYDROXYLATION; REACTION ANALYSIS; RING OPENING; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 33749037979     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060949p     Document Type: Article

References (40)

1. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
2. Park, C. Y.; Kim, B. M.; Sharpless, K. B. Tetrahedron. Lett. 1991, 32, 1003.
3. Ahmed, Md. M.; O'Doherty, G. A. J. Org. Chem. 2005, 70, 10576.
4. Ahmed, Md. M.; Berry, B. P.; Hunter, D. J.; Tomcik, D. J.; O'Doherty, G. A. Org. Lett. 2005, 7, 745.
5. (a) Herz, W.; Ligon, R. C.; Turner, J. A.; Blount, J. F. J. Org. Chem. 1977, 42, 1885.
6. (b) Boyd, J. D.; Foote, C. S.; Imagawa, D. K. J. Am. Chem. Soc. 1980, 102, 3641.
7. (c) Suzuki, M.; Noyori, R.; Hamanaka, N. J. Am. Chem. Soc. 1981, 103, 5606.
8. (d) Balci, M.; Sutbeyaz, Y. Tetrahedron Lett. 1983, 24, 4135.
9. (e) Harter, R.; Weymuth, C.; Scheffold, R.; Engel, P.; Linden, A. Helv. Chim. Acta 1993, 76, 353.
10. (f) Avery, T. D.; Jenkins, N. F.; Kimber, M. C.; Lupton, D. W.; Taylor, D. K. Chem. Commun. 2002, 28.
11. Schulz, M.; Kluge, R.; Liebsch, S.; Lessig, J.; Halik, M.; Gadissa, F. Tetrahedron 1996, 52, 13151.
12. Jefford, C. W.; Misra, D.; Dishington, A. P.; Timari, G.; Rossier, J.; Bernardinelli, G. Tetrahedron Lett. 1994, 35, 6275.
13. Suzuki, M.; Ohtake, H.; Kameya, Y.; Hamanaka, N.; Noyori, R. J. Org. Chem. 1989, 54, 5292.
14. Matsumoto, M.; Dobashi, S.; Kuroda, K.; Kondo, K. Tetrahedron 1985, 41, 2147.
15. Wang, Z.; Kakiuchi, K.; Sharpless, K. B. J. Org. Chem. 1994, 59, 6895.
16. Andersson, P. G.; Sharpless, K. B. J. Am. Chem. Soc. 1993, 115, 7047.
17. Jacobsen, E. N.; Marko, I.; France, M. B.; Svendsen, J. S.; Sharpless, K. B. J. Am. Chem. Soc. 1989, 111, 737.
18. (a) Schneider, W. P.; McIntosh, A. V. U.S. Patent 2, 769,824, Nov. 6, 1956.
19. (b) VanRheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 17, 1973.
20. Kornblum, N.; DeLaMare, H. E. J. Am. Chem. Soc. 1951, 73, 880.
21. Dupau, P.; Epple, R.; Thomas, A. A.; Fokin, V. V.; Sharpless, K. B. Adv. Synth. Catal. 2002, 344, 421.
22. Hoffman, K. A.; Chem. Ber. 1912, 45, 3329.
23. Schroder, M. Chem. Rev. 1980, 80, 187.
24. Endo, K.; Seya, K.; Hikino, H. Tetrahedron 1987, 43, 2681.
25. Adam, W.; Klug, G.; Peters, E. M.; Peters, K.; Von Schnerring, H. G. Tetrahedron 1985, 41, 2045.
26. Campagnole, M.; Bourgeois, M. J.; Montaudon, E. Tetrahedron 2002, 58, 1165.
27. Kropf, H. In Houben-Weyl Methoden der Organischen Chemie, Peroxo-Verbindungen (Houben-Weyl Methods of Organic Chemistry, Peroxo-Connections); Kropf, H., Ed.; Thieme: Stuttgart, Germany, 1988; pp 1102-1116.
28. Dai, P.; Dussault, P. H.; Trullinger, T. K. J. Org. Chem. 2004, 69, 2851.
29. Kara, Y.; Balci, M. Tetrahedron 2003, 59, 2063.
30. Ikawa, T.; Sajiki, H.; Hirota, K. Tetrahedron 2004, 60, 6189.
31. Weisburger, J. H.; Griswold, D. P.; Prejean, J. D.; Casey, A. E.; Wood, H. B.; Weisburger, E. K. Recent Results Cancer Res. 1975, 52, 1.
32. Chiuten, D. F.; Rozencweig, M.; Von Hoff, D. D.; Muggia, F. M. Cancer 1981, 47, 442.
33. Angyal, S. J.; Le Fur, R. Carbohydr. Res. 1980, 84, 201.
34. Greatrex, B. W.; Jenkins, N. F.; Taylor, D. K.; Tiekink, E. R. T. J. Org. Chem. 2003, 68, 5205.
35. Angyal, S. J.; Bethell, G. S. Aust. J. Chem. 1976, 29, 1249.
36. Angyal, S. J.; Bethell, G. S.; Cowley, D. E. Aust. J. Chem. 1976, 29, 1239.
37. Kaufmann, H.; Reichstein, T. Helv. Chim. Acta 1967, 50, 2280.
38. Lett, R.; Bory, S.; Moreau, B.; Marquet, A. Bull. Soc. Chim. Fr. 1972, 6, 2299.
39. Coffey, S. Rodd's Chemistry of Carbon Compounds, 2nd ed.; Elsevier Publishing Company: Amsterdam, The Netherlands, 1967; Vol. 1F, p 19.
40. Suh, H.; Wilcox, C. S. J. Am. Chem. Soc. 1988, 110, 470.