A tandem oxidation procedure for the conversion of alcohols into 1,1-dibromoalkenes

Synlett

Volumn , Issue 5, 2004, Pages 819-822

  Raw, Steven A ^a   Reid, Mark ^a   Roman, Estelle ^a   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

Dibromoalkenes; MTBD; One pot; Tandem oxidation procedure

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; IMIDAZOLE DERIVATIVE;

ARTICLE; OXIDATION;

EID: 1942489358     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-820027     Document Type: Article

References (31)

1. Huh, D. H.; Jeong, J. S.; Lee, H. B.; Ryu, H.; Kim, Y. G. Tetrahedron 2002, 58, 9925.
2. (2) For some noteworthy examples in natural product synthesis see: (a) Roush, W. R.; Brown, B. B. J. Org. Chem. 1993, 58, 2162. (b) Meyers, A. G.; Hogan, P. C.; Hurd, A. R.; Goldberg, S. D. Angew. Chem. Int. Ed. 2002, 41, 1104. (c) Evans, D. A.; Starr, J. T. Angew. Chem. Int. Ed. 2002, 41, 1865. (d) Mergott, D. J.; Frank, S. A.; Roush, W. R. Org. Lett. 2002, 4, 3157.
3. For some noteworthy examples in natural product synthesis see: (a) Roush, W. R.; Brown, B. B. J. Org. Chem. 1993, 58, 2162. (b) Meyers, A. G.; Hogan, P. C.; Hurd, A. R.; Goldberg, S. D. Angew. Chem. Int. Ed. 2002, 41, 1104. (c) Evans, D. A.; Starr, J. T. Angew. Chem. Int. Ed. 2002, 41, 1865. (d) Mergott, D. J.; Frank, S. A.; Roush, W. R. Org. Lett. 2002, 4, 3157.
4. For some noteworthy examples in natural product synthesis see: (a) Roush, W. R.; Brown, B. B. J. Org. Chem. 1993, 58, 2162. (b) Meyers, A. G.; Hogan, P. C.; Hurd, A. R.; Goldberg, S. D. Angew. Chem. Int. Ed. 2002, 41, 1104. (c) Evans, D. A.; Starr, J. T. Angew. Chem. Int. Ed. 2002, 41, 1865. (d) Mergott, D. J.; Frank, S. A.; Roush, W. R. Org. Lett. 2002, 4, 3157.
5. For some noteworthy examples in natural product synthesis see: (a) Roush, W. R.; Brown, B. B. J. Org. Chem. 1993, 58, 2162. (b) Meyers, A. G.; Hogan, P. C.; Hurd, A. R.; Goldberg, S. D. Angew. Chem. Int. Ed. 2002, 41, 1104. (c) Evans, D. A.; Starr, J. T. Angew. Chem. Int. Ed. 2002, 41, 1865. (d) Mergott, D. J.; Frank, S. A.; Roush, W. R. Org. Lett. 2002, 4, 3157.
6. Uenishi, J.; Kawahama, R.; Yonemitsu, O. J. Org. Chem. 1998, 63, 8965.
7. Kuang, C.; Senboku, H.; Tokuda, M. Tetrahedron 2002, 58, 1491.
8. Lee, H. B.; Huh, D. H.; Oh, J. S.; Min, G.-H.; Kim, B. H.; Lee, D. H.; Hwang, J. K.; Kim, Y. G. Tetrahedron 2001, 57, 8283.
9. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 13, 3769.
10. Lin, S.-T.; Lee, C.-C.; Liang, D. W. Tetrahedron 2000, 56, 9619.
11. Ramirez, F.; Desai, N. B.; McKelvie, N. J. Am. Chem. Soc. 1962, 84, 1745.
12. 11 and could be stored on the bench for several months without any noticeable degradation, either by NMR spectroscopy or in its reactivity.
13. Patrick, M.; Gennet, D.; Rassat, A. Tetrahedron Lett. 1999, 40, 8575.
14. Dolhem, F.; Lièvre, C.; Demailly, G. Tetrahedron Lett. 2002, 43, 1847.
15. Korotchenko, V. N.; Shastin, A. V.; Nenajdenko, V. G.; Balenkova, E. S. Org. Biomol. Chem. 2003, 1, 1906.
16. Baxendale, I. R.; Ley, S. V.; Sneddon, H. F. Synlett 2002, 775.
17. (a) Blackburn, L.; Wei, X.; Taylor, R. J. K. Chem. Commun, 1999, 1337,
18. (b) Wei, X.; Taylor, R. J. K. J. Org. Chem. 2000, 65, 616.
19. (c) Blackburn, L.; Kanno, H.; Taylor, R. J. K. Tetrahedron Lett. 2003, 44, 115.
20. (d) Outram, H. S.; Raw, S. A.; Taylor, R. J. K. Tetrahedron Lett. 2002, 43, 6185.
21. (a) Blackburn, L.; Pei, C.; Taylor, R. J. K. Synlett 2002, 215.
22. (b) Reid, M.; Rowe, D.; Taylor, R. J. K. Chem. Commun. 2003, 2284.
23. (a) Davies, S. B.; McKervey, M. A. Tetrahedron Lett. 1999, 40, 1229.
24. (b) Nicolaou, K. C.; Li, Y.; Fylaktakidou, K. C.; Mitchell, H. J.; Wei, H.-X.; Weyershausen, B. Angew. Chem. Int. Ed. 2001, 40, 3849.
25. (c) Mladenova, M.; Tavlinova, M.; Momchev, M.; Alami, M.; Ourévitch, M.; Brion, J. D. Eur. J. Org. Chem. 2003, 2713.
26. (d) Nicolaou, K. C.; Li, Y.; Fylaktakidou, K. C.; Monenschein, H.; Li, Y.; Weyershausen, B.; Mitchell, H. J.; Wei, H.-X.; Guntupalli, P.; Hepworth, D.; Sugita, K. J. Am. Chem. Soc. 2003, 725, 15433.
27. Simoni, D.; Rossi, M.; Rondanin, R.; Mazzani, A.; Baruchello, C.; Malagutti, C.; Roberti, M.; Indiviata, F. P. Org. Lett. 2000, 2, 3765.
28. 2 or chloroform; 10 mL) was added MTBD 3 (0.22 mL, 1.50 mmol). The reaction mixture was heated at reflux for 30 min, cooled to r.t., then a solution of alcohol (1 mmol) in solvent (5 mL) added. The reaction mixture was then heated at reflux for the time specified, cooled to r.t. and filtered through Celite®. The resulting filtrate was then pre-loaded on to silica and the dibromoalkenes purified by silica chromatography, eluting with EtOAc/petroleum ether.
29. Bestmann, H. J.; Frey, H. Liebigs Ann, Chem. 1980, 12, 2061.
30. Lok, W. N.; Ward, A. D. Aust. J. Chem. 1978, 31, 617.
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