Controlled Garegg conditions for selective iodination on pyranose templates

European Journal of Organic Chemistry

Volumn , Issue 12, 2011, Pages 2286-2292

  Simao, Ana Catarina ^a   Silva, Sandrina ^a   Rauter, Amelia P ^b   Rollin, Patrick ^a   Tatibouët, Arnaud ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

^b UNIVERSITY OF LISBON   (Portugal)

Author keywords

Carbohydrates; Halogenation; Iodination; Synthetic methods

Indexed keywords

EID: 79953697726     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201001325     Document Type: Article

References (30)

1. J. E. G. Barnett, Adv. Carbohydr. Chem. Biochem. 1967, 22, 177-227.
2. W. A. Szarek, Adv. Carbohydr. Chem. Biochem. 1973, 28, 225-306.
3. A. R. Vaino, W. A. Szarek, Adv. Carbohydr. Chem. Biochem. 2000, 56, 9-63.
4. B. R. Castro, Org. React. 1983, 29, 1-62.
5. P. J. Garegg, Pure Appl. Chem. 1984, 56, 845-858.
6. P. J. Garegg, B. Samuelsson, J. Chem. Soc., Chem. Commun. 1979, 978-980.
7. P. J. Garegg, B. Samuelsson, J. Chem. Soc. Perkin Trans. 1 1980, 2866-2869.
8. P. R. Skaanderup, C. S. Poulsen, L. Hyldtoft, M. R. Jorgensen, R. Madsen, Synthesis 2002, 1721-1727.
9. A. R. Ellwood, M. J. Porter, J. Org. Chem. 2009, 74, 7982-7985.
10. A. Tatibouët, M. Lefoix, J. Nadolny, O. R. Martin, P. Rollin, J. Yang, G. D. Holman, Carbohydr. Res. 2001, 333, 327-334.
11. I. Izquierdo, M. T. Plaza, V. Yanez, Tetrahedron 2007, 63, 1440-1447.
12. P. J. Garegg, B. Samuelsson, Synthesis 1979, 813-814.
13. F. W. Lichtenthaler, W. Doleschal, S. Hahn, Liebigs Ann. Chem. 1985, 2454-2464.
14. A. C. Simao, A. Tatibouët, A. P. Rauter, P. Rollin, Tetrahedron Lett. 2010, 51, 4602-4604.
15. K. Weinges, S. Haremsa, W. Maurer, Carbohydr. Res. 1987, 164, 453-458.
16. I. Dancy, L. Laupichler, P. Rollin, J. Thiem, Liebigs Ann. Chem. 1993, 343-350.
17. I. Izquierdo, M. T. Plaza, M. Rodriguez, J. A. Tamayo, A. Martos, Tetrahedron 2006, 62, 2693-2697.
18. M. I. Garcia-Moreno, M. Aguilar, C. Ortiz Mellet, J. M. Garcia Fernandez, Org. Lett. 2006, 8, 297-299 and references cited therein.
19. J. Kang, G. J. Lim, S. K. Yoon, M. Y. Kim, J. Org. Chem. 1995, 60, 564-577.
20. A. Tatibouët, J. Yang, C. Morin, G. D. Holman, Bioorg. Med. Chem. 2000, 8, 1825-1833.
21. I. Izquierdo, M. T. Plaza, M. Rodriguez, F. Franco, A. Martos, Tetrahedron 2005, 61, 11697-11704 and references cited therein.
22. I. Izquierdo Cubero, M. T. Plaza Lopez-Espinosa, An. Quim. 1990, 86, 554-560.
23. E. Kaji, E. Kurimoto, R. Saiga, A. Matsuura, K. Harada, T. Nishino, Heterocycles 2005, 66, 453-468.
24. N. Nakajima, M. Matsumoto, M. Kirihara, M. Hashimoto, T. Katoh, S. Terashima, Tetrahedron 1996, 52, 1177-1194.
25. P. C. M. Hervé du Penhoat, A. S. Perlin, Carbohydr. Res. 1979, 71, 149-167.
26. H. H. Brandstetter, E. Zbiral, Helv. Chim. Acta 1980, 63, 327-343.
27. M.-K. Chung, G. Orlova, J. D. Goddard, M. Schlaf, R. Harris, T. J. Beveridge, G. White, F. R. Hallett, J. Am. Chem. Soc. 2002, 124, 10508-10518.
28. V. Belakhov, E. Dovgolevsky, E. Rabkin, S. Shulami, Y. Shoham, T. Baasov, Carbohydr. Res. 2004, 339, 385-392.
29. D. J. Chambers, G. R. Evans, A. Fairbanks, Tetrahedron 2005, 61, 7184-7192.
30. D. D. Perrin, W. L. F. Armarego, D. R. Perrin, Purification of Laboratory Chemicals, Pergamon, Oxford, 1986.