NaIO4/LiBr-mediated diastereoselective dihydroxylation of olefins: A catalytic approach to the prevost-woodward reaction

Organic Letters

Volumn 7, Issue 22, 2005, Pages 5071-5074

  Emmanuvel, Lourdusamy ^a   Ali Shaikh, Tanveer Mahammad ^a   Sudalai, Arumugam ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 27644433520     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052080n     Document Type: Article

References (35)

1. (a) Hudlicky, M. Oxidations in Organic Chemistry; ACS Monograph Series 186; American Chemical Society: Washington, DC, 1990; pp 174.
2. (b) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, WeinHein, 2000; p 357.
3. (c) Haines, A. H. Comprehensive Organic Synthesis, 1st ed.; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 7, p 437.
4. (a) Criegee, R. Justus Liebigs Ann. Chem. 1936, 522, 75.
5. (b) Criegee, R.; Marchand, B.; Wannowius, H. Justus Liebigs Ann. Chem. 1942, 550, 99.
6. (c) Schroder, M. Chem. Rev. 1980, 80, 187.
7. (d) Hentges, S. G.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 4263.
8. (e) Nomura, K.; Okazaki, K.; Hori, K.; Yoshii, E. J. Am. Chem. Soc. 1987, 109, 3402.
9. (f) Coleman, J. E.; Ricciuti, C.; Swern, D. J. Am. Chem. Soc. 1956, 78, 5342.
10. (g) Ogino, T. Tetrahedron Lett. 1980, 21, 177.
11. (h) Weber, W, P.; Shepherd, J, P. Tetrahedron Lett. 1972, 13, 4907.
12. (i) Ogino, T.; Mochizuki, K. Chem. Lett. 1979, 4.
13. (j) Plietker, B.; Niggemann, M. J. Org. Chem. 2005, 70, 2402 and references therein.
14. (k) Ho, C. M.; Yu, W.-Y.; Che, C.-M. Angew. Chem., Int. Ed. 2004, 43, 3303.
15. (a) Woodward, R. B.; Brutcher, F. V. J. Am. Chem. Soc. 1958, 80, 209.
16. (b) Woodward, R. B. U.S. Patent, 2,687,435, 1954.
17. (c) House, H. E. Modern Synthetic Reactions, 2nd ed.; Benjamin: Menlo Park, CA, 1972; p 439.
18. Plesnicar, B. Oxidations in Organic Chemistry; Trahanovsky, W. S., Ed.; Academic Press: New York, 1978; Part C, p 211.
19. (a) Prevost, C. Compt. Rend. 1933, 196, 1129.
20. Prevost, C. Compt. Rend. 1933, 197, 1661.
21. (b) Prevost, C.; Wiemann, J. Compt. Rend. 1937, 204, 700.
22. (c) Cambie, R. C.; Rutledge, P. S. Org. Synth. 59, 169.
23. (a) Uemura, S.; Ohe, K.; Fukuzawa, S.; Patil, S.; Sugita, N. J. Organomet. Chem. 1986, 316, 67.
24. (b) Georgoulis, C.; Valery, J. Bull. Soc. Chim. Fr. 1975, 1431.
25. (c) Georgoulis, C.; Valery, J. Synthesis 1978, 402.
26. (d) Horiuchi, C. A.; Satoh, J, Y. Bull. Chem. Soc. Jpn. 1987, 60, 426.
27. (e) Cambie, R. C.; Hayward, R. C.; Roberts, J. L.; Rutledge, P. S. J. Chem. Soc., Perkin Trans. 1 1974, 1858.
28. (f) Buddrus, J. Angew. Chem., Int. Ed. Engl. 1973, 12, 163.
29. (g) Corey, E. J.; Das, J. Tetrahedron Lett. 1982, 23, 4217.
30. (a) Dewkar, G. K.; Narina, S. V.; Sudalai, A. Org. Lett. 2003, 5, 4501.
31. (b) Shaikh, T. M.; Sudalai, A. Tetrahedron. Lett. 2005, 46, 5589.
32. Bergman, J.; Engman, L. J. Org. Chem. 1982, 47, 5191.
33. 4 and concentrated under reduced pressure to give crude diol, which was purified by column chromatography packed with silica gel using pet ether and EtOAc (7:3) as eluents to afford pure diol.
34. Cyclic voltammogram is given in Supporting Information.
35. 2. Octyl bromide failed to undergo oxidation under the same reaction condition. Hence, we believe that neighboring group participation by the acetate group makes the C-Br bond more polar and thus facilitating the oxidation process.