Recycling of osmium catalyst in oxidative olefin cleavage: A chemoentrapment approach

Tetrahedron Letters

Volumn 52, Issue 12, 2011, Pages 1363-1367

  Kim, Seyoung ^a   Chung, Jooyoung ^a   Kim, B Moon ^a  

^a Seoul National University   (South Korea)

Author keywords

Catalyst recycle; Chemoentrapment; Lemieux Johnson; Olefin cleavage; Osmium tetroxide

Indexed keywords

ACETONITRILE; ALKENE; OSMIUM; POTASSIUM HYDROXIDE; SODIUM CHLORIDE; SODIUM IODIDE; WATER;

ARTICLE; CATALYST; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION; REACTION ANALYSIS; REACTION OPTIMIZATION; RECYCLING; SCREENING;

EID: 79951771114     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.01.065     Document Type: Article

References (28)

1. Travis, B. R.; Narayan, R. S.; Borhan, B. J. Am. Chem. Soc. 2002, 124, 3824.
2. (a) Kobayashi, S.; Endo, M.; Nagayama, S. J. Am. Chem. Soc. 1999, 121, 11229;
3. (b) Kobayashi, S.; Ishida, T.; Akiyama, R. Org. Lett. 2001, 3, 2649;
4. (c) Ley, S. V.; Ramarao, C.; Lee, A.; Østergaard, N.; Smith, S. C.; Shirley, I. M. Org. Lett. 2003, 5, 185;
5. (d) Ishida, T.; Akiyama, R.; Kobayashi, S. Adv. Synth. Catal. 2003, 345, 576;
6. (e) Ishida, T.; Akiyama, R.; Kobayashi, S. Adv. Synth. Catal. 2005, 347, 1189.
7. (a) Sevreyns, A.; De Vos, D. E.; Fiermans, L.; Verpoort, F.; Grobet, P. G.; Jacobs, P. A. Angew. Chem., Int. Ed. 2001, 40, 586;
8. (b) Yang, J. W.; Han, H.; Roh, E. J.; Lee, S. G.; Song, C. E. Org. Lett. 2002, 4, 4685.
9. (a) Choudary, B. M.; Chowdari, N. S.; Kantam, M. L.; Raghavan, K. V. J. Am. Chem. Soc. 2001, 123, 9220;
10. (b) Choudary, B. M.; Chowdari, N. S.; Jyothi, K.; Kantam, M. L. J. Am. Chem. Soc. 2002, 124, 5341.
11. (a) Song, C. E.; Jung, D.; Roh, E. J.; Lee, S.; Chi, D. Y. Chem. Commun. 2002, 3038;
12. (b) Branco, L. C.; Afonso, C. A. M. Chem. Commun. 2002, 3036;
13. (c) Branco, L. C.; Afonso, C. A. M. J. Org. Chem. 2004, 69, 4381.
14. Lee, D.; Lee, H.; Kim, S.; Yeom, C.-E.; Kim, B. M. Adv. Synth. Catal. 2006, 348, 1021.
15. Whitehead, D. C.; Travis, B. R.; Borhan, B. Tetrahedron Lett. 2006, 47, 3797.
16. Johnson, R. A. In Catalytic asymmetric dihydroxylation discovery and development Catalytic Asymmetric Synthesis; Ojima, I., Sharpless, K. B., Eds.; VCH: New York, 2000; pp 357-398.
17. Pappo, R.; Allen, D. S.; Lemieux, R. U.; Johnson, W. S. J. Org. Chem. 1956, 21, 478.
18. Somaiah, P. V.; Reddy, K. B.; Sethuram, B.; Rao, T. N. Indian J. Chem., Sect A. EN 1988, 27, 876.
19. When olefin cleavage was performed stilbene diol as the starting material under the same basic reaction conditions, only 75% of benzaldehyde was obtained after 24 hours.
20. Geng, X.-L.; Wang, Z.; Li, X.-Q.; Zhang, C. J. Org. Chem. 2005, 70, 9610.
21. Junttila, M. H.; Hormi, O. E. O. J. Org. Chem. 2004, 69, 4816.
22. (a) Hirano, M.; Yakabe, S.; Clark, J. H.; Kudo, H.; Morimoto, T. Synth. Commun. 1996, 26, 1875;
23. (b) Hirano, M.; Yakabe, S.; Clark, J. H.; Morimoto, T. J. Chem. Soc., Perkin Trans. 1 1996, 2693.
24. Zhao, M.; Li, J.; Mano, E.; Song, Z.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. Org. Chem. 1999, 64, 2564.
25. Besemer, A. D. European Patent 1341717, 2004.
26. (a) Carlsen, H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936;
27. (b) Rossiter, B. E.; Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 464.
28. 4, and filtered. The organic solution was directly analyzed with HPLC after addition of an internal standard or purified by flash column chromatography to yield the desired product.