Mild oxidative one-pot allyl group cleavage

Organic Letters

Volumn 3, Issue 18, 2001, Pages 2835-2838

  Kitov, Pavel I ^a   Bundle, David R ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0000483537     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016278t     Document Type: Article

References (31)

1. Gent, P. A.; Gigg, R. Carbohydr. Res. 1976, 49, 325-333. Rollin, P.; Sinay, P. J. Chem. Soc., Perkin Trans. 1 1977, 2513-2517.
2. Gent, P. A.; Gigg, R. Carbohydr. Res. 1976, 49, 325-333. Rollin, P.; Sinay, P. J. Chem. Soc., Perkin Trans. 1 1977, 2513-2517.
3. Warren, C. D.; Jeanloz, R. W. Carbohydr. Res. 1977, 53, 67-84.
4. Boss, R.; Scheffold, R. Angew. Chem., Int. Ed. Engl. 1976, 15, 558-559.
5. Ogawa, T.; Nakabayashi, S.; Kitajima, T. Carbohydr. Res. 1983, 114, 225-236. Smith, A. B.; Rivero, R. A.; Hale, K. J.; Vaccaro, H. A. J. Am. Chem. Soc. 1991, 113, 2042-2112.
6. Ogawa, T.; Nakabayashi, S.; Kitajima, T. Carbohydr. Res. 1983, 114, 225-236. Smith, A. B.; Rivero, R. A.; Hale, K. J.; Vaccaro, H. A. J. Am. Chem. Soc. 1991, 113, 2042-2112.
7. Nicolaou, K. C.; Hummel, C. W.; Bockovich, N. J.; Wong, C.-H. J. Chem. Soc., Chem. Commun. 1991, 870-872.
8. Oltvoort, J. J.; van Boeckel, C. A. A.; de Koning, J. H.; van Boom, J. H. Synthesis 1981, 305-308. Hecker, S. J.; Minich, M. L.; Lackey, K. J. Org. Chem. 1990, 55, 4904-4911.
9. Oltvoort, J. J.; van Boeckel, C. A. A.; de Koning, J. H.; van Boom, J. H. Synthesis 1981, 305-308. Hecker, S. J.; Minich, M. L.; Lackey, K. J. Org. Chem. 1990, 55, 4904-4911.
10. Yadav, J. S.; Chandrasekhar, S.; Sumithra, G.; Kache, R. Tetrahedron Lett. 1996, 37, 6603-6606.
11. Kariyone, K.; Yazawa, H. Tetrahedron Lett. 1970, 2885-2888.
12. Diaz, R. R.; Melgarejo, C. R.; Lopez-Espinosa, M. T. P.; Cubero, I. I. J. Org. Chem. 1994, 59, 7928-7929.
13. Roy, R.; Tropper, F. D. J. Chem. Soc., Chem. Commun. 1988, 15, 1058-1060. Ramos, D.; Rollin, P.; Klaffke, W. Angew. Chem., Int. Ed. 2000, 39 (2), 396-398. Yudina, O. N.; Sherman, A. A.; Nifantiev, N. E. Carbohydr. Res. 2001, 332, 363-371.
14. Roy, R.; Tropper, F. D. J. Chem. Soc., Chem. Commun. 1988, 15, 1058-1060. Ramos, D.; Rollin, P.; Klaffke, W. Angew. Chem., Int. Ed. 2000, 39 (2), 396-398. Yudina, O. N.; Sherman, A. A.; Nifantiev, N. E. Carbohydr. Res. 2001, 332, 363-371.
15. Roy, R.; Tropper, F. D. J. Chem. Soc., Chem. Commun. 1988, 15, 1058-1060. Ramos, D.; Rollin, P.; Klaffke, W. Angew. Chem., Int. Ed. 2000, 39 (2), 396-398. Yudina, O. N.; Sherman, A. A.; Nifantiev, N. E. Carbohydr. Res. 2001, 332, 363-371.
16. Kitov, P. I.; Bundle, D. R. J. Chem. Soc., Perkin Trans. 1 2001, 8, 838-853.
17. Gigg, J.; Gigg, R.; Payne, S.; Conant, R. J. Chem. Soc., Perkin Trans. 1 1987, 1165-1170.
18. Dolbler, C.; Mehltretter, G. M.; Sundermeier, U.; Beller, M. J. Am. Chem. Soc. 2000, 122, 10289-10297.
19. Koike, K.; Sugimoto, M.; Sato, S.; Ito, Y.; Nakahara, Y.; Ogawa, T. Carbohydr. Res. 1987, 163, 189-208.
20. Nilsson, U.; Ray, A. K.; Magnusson, G. Carbohydr. Res. 1994, 252, 117-136.
21. Suhr, R.; Scheel, O.; Thiem, J. J. Carbohydr. Chem. 1998, 17 (6), 937-968.
22. Sabesan, S.; Lemieux, R. U. Can. J. Chem. 1984, 62, 644-654.
23. Ziegler, T.; Eckhardt, E.; Strayle, J.; Herzog, H. Carbohydr. Res. 1994, 253 (1), 167-184.
24. Mereyala, H. B.; Gurrala, S. R.; Mohan, S K. Tetrahedron 1999, 55 (37), 11331-11342.
25. Spevak, W.; Dasgupta, F.; Hobbs, C. J.; Nagy, J. O. J. Org. Chem. 1996, 61 (10), 3417-3422.
26. Takeo, K.; Maki, K.; Wada, Y.; Kitamura, S. Carbohydr. Res. 1993, 245 (1), 81-96.
27. Knerr, L.; Pannecoucke, X.; Luu, B. Tetrahedron Lett. 1998, 39 (3-4), 273-274.
28. Jansson, K.; Frejd, T.; Kihlberg, J.; Magnusson, G. Tetrahedron Lett. 1988, 29 (3), 361-362.
29. Stevens, J. D. In Methods in Carbohydrate Chemistry; Whistler, R. L., BeMiller, J. N., Eds.; Academic Press: New York and London, 1972; Vol. VI, Chapter 16, pp 124-125.
30. Priya, K.; Loganathan, D. Tetrahedron 1999, 55 (4), 1119-1128.
31. 4 (3 equiv, 431 mg) in water (5 mL). The mixture was stirred at 60°C for 3 h and then diluted with brine and extracted with DCM. Chromatography on silica gel with hexanes - ethyl acetate (8:2-6:4) gave formate 4 (18 mg, 4.6%) and 2,3,4,6-tetra-O-benzyl-D-galactopyranose 5 (275 mg, 75%).