Iodine(III)-initiated bromoacetoxylation of olefins

Synlett

Volumn , Issue 2, 1998, Pages 195-197

  Hashem, Md Abul ^a,b   Jung, Alexander ^a   Ries, Monika ^a   Kirschning, Andreas ^a  

^a CLAUSTHAL UNIVERSITY OF TECHNOLOGY   (Germany)

^b JAHANGIRNAGAR UNIVERSITY   (Bangladesh)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 26844537398     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1596     Document Type: Article

References (21)

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3. (c) Stang, P. J., Zhdankin, V. V., Chem. Rev., 1996, 96, 1123-1178.
4. (d) Varvoglis, A., Hypervalent Iodine in Organic Synthesis, Acadamic Press, San Diego, London, 1997.
5. Kirschning, A., Plumeier, C., Rose, L., Chem. Commun. 1997, in press.
6. de Armas, P., Concepción, J. I., Francisco, C. G., Hernández, R, Salazar, J. A., Suárez, E. J. Chem. Soc., Perkin Trans. I, 1989, 405-411.
7. Szántay, C., Blaskó, G., Bárczai-Beke, M., Péchy, P., Dörnei, G., Tetrahedron Lett., 1980, 21, 3509-3512.
8. A similar species may be involved in the haloacetoxylation of dimethoxynaphtalenes: (a) Evans, P. A., Brandt, T. A., Tetrahedron Litt., 1996, 37, 6443-6446.
9. (b) Evans, P. A., Brandt, T. A., J. Org. Chem., 1997, 62, 5321-5326.
10. For a review on cohalogenations see: Rodriguez, J., Dulcère, J.-P., Synthesis, 1993, 1177-1205.
11. 2, gave similar diastereomeric ratios. However, the reaction was only complete after more than one to two days and the α-bromoacetates were isolated in slightly reduced yields (48-54 %).
12. 3).
13. +]. For additional data on unsaturated sugars like 12a refer to: Harders, J., Garming, A., Jung, A., Kaiser, V., Monenschein, H., Ries, M., Rose, L., Schöning, K.-U., Weber, T., Kirschning, A., Liebigs Ann. Chem., 1997, 2125-2132.
14. Roush, W. R., Briner, K., Sebesta, D. P. Synlett, 1993, 264-266.
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16. Lafont, D., Boullanger, P., Carvalho, F., Vottero, P., Carbohydr. Res., 1997, 297, 117-226 and references cited therein.
17. For reviews on 2-deoxygenated oligosaccharides see: (a) Kirschning, A., Bechthold, A., Rohr, J. Top. Curr. Chem., 1997, 188, 1-88.
18. (b) Danishefsky, S. J., Bilodeau, M. T., Angew. Chem., 1996, 108, 1482-1522;
19. Angew. Chem. Int. Ed. Engl., 1996, 35, 1380-1419.
20. (c) Kennedy, J. F., White, C. A., Bioactive Carbohydrates in Chemistry, Biochemistry, and Biology, Ellis Horwood, Chichester, 1983.
21. 3).