Development of a new triphase catalyst and its application to the epoxidation of allylic alcohols

Organic Letters

Volumn 3, Issue 12, 2001, Pages 1837-1840

  Yamada, Yoichi M A ^a   Ichinohe, Masato ^a   Takahashi, Hideyo ^a   Ikegami, Shiro ^a  

^a TEIKYO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0000639066     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015863r     Document Type: Article

References (41)

1. Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: Oxford, 1998.
2. Regen, S. L. Angew. Chem., Int. Ed. Engl. 1979, 18, 421-429.
3. (a) Bunin, B. A. The Combinatorial Index; Academic Press: San Diego, 1998.
4. (b) Reactions on Polymers; Moore, J. A. Ed.; Redel: Boston, 1973.
5. (c) Solid-Phase Synthesis; Blossey, E. C., Neckers, D. C., Eds.; Dowden, Hutchinson and Ross: Stroudsburg, PA, 1975.
6. Recent selected examples for improvement on surfactant-supported catalysts: (a) Manabe, K.; Mori, Y.; Wakabayashi, T.; Nagayama, S.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 7202-7207.
7. On microencapsulated catalysts: (b) Kobayashi, S.; Endo, M.; Nagayama, S. J. Am. Chem. Soc. 1999, 121, 11229-11230.
8. On the catalyst immobilized on a polystyrenepoly(ethylene glycol)-grafted polymer resin: (c) Shibatomi, K.; Nakahashi, T.; Uozumi, Y. Synlett 2000, 1643-1645.
9. (d) Uozumi, Y.; Watanabe, T. J. Org. Chem. 1999, 64, 6921-6923.
10. For a PEG-supported phase transfer catalyst: (e) Annuziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Tocco, G. Org. Lett. 2000, 2, 1737-1379.
11. For reviews: (f) Totten, G. E.; Clinton, N. A.; Matlock, P. L. J. Macromol. Sci., Rev. Macromol. Chem. Phys. 1998, C38, 77-142.
12. (g) Desikan, S.; Doraiswamy, L. K. Ind. Eng. Chem. Res. 1995, 34, 3524-3537.
13. For reviews on supramolecular complex: (a) Lehn, J.-M. Supramolecular Chemistry: VCH: Verlagsgesellschaft, 1995.
14. (b) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319.
15. Self-assembly of colloidal gold and a polymer: (c) Boal, A. K.; Ilhan, F.; DeRouchey, J. E.; Thurn-Albrecht, T.; Russell, T. P.; Rotello, V. M. Nature 2000, 404, 746-748.
16. Self-assembly of complementary random copolymers: (d) Muthukumar, M.; Ober, C. K.; Thomas, E. L. Science 1997, 277, 1225-1232.
17. (e) Ilhan, F.; Galow, T. H.; Gray, M.; Clavier, G.; Rotello, V. M. J. Am. Chem. Soc. 2000, 122, 5895-5896.
18. 3 for excellent insoluble Lewis-acidic catalyst: (f) Reetz, M. T.; Giebel, D. Angew. Chem., Int. Ed. 2000, 39, 2498-2501.
19. On excellent biphenolate catalysts cross-linked by aluminum in an organic solvent: (g) Saito, S.; Murase, M.; Yamamoto, H. Synlett 1999, 57-58.
20. (h) Arai, T.; Hu, Q.-S.; Zheng, X.-F.; Pu, L.; Sasai, H. Org. Lett. 2000, 2, 4261-4263.
21. 4.
22. (b) Sato, K.; Aoki, M.; Noyori, R. Science 1998, 281, 1646-1647.
23. Other selected examples on tungsten-catalyzed oxidations, see: (c) Venturello, C.; Gambaro, M. J. Org. Chem. 1991, 50, 5924-5931.
24. (d) Venturello, C.; Gambaro, M. Synthesis 1989, 295-297.
25. (e) Bortolini, O.; Conte, V.; Di Furia, F.; Modena, G. J. Org. Chem. 1986, 51, 2661-2663.
26. (f) Ishii, Y.; Yamawaki, K.; Ura, T.; Yamada, H.; Yoshida, T.; Ogawa, M. J. Org. Chem. 1988, 53, 3587-3593.
27. For recent attempts to improve the drawbacks on polymer-supported tungsten catalysts, see: (a) Villa, A. L.; Sels, B. F.; de Vos, D. E.; Jacobs, P. A. J. Org. Chem. 1999, 64, 7267-7270.
28. (b) Hoegaerts, D.; Sels, B. F.; de Vos, D. E.; Verpoort, F.; Jacobs, P. A. Catal. Today 2000, 60, 209-218.
29. (c) Gelbard, G.; Breton, F.; Quenard, M. Sherrington, D. C. J. Mol. Catal. A: Chem 2000, 153, 7-18.
30. (d) Sakamoto, T.; Pac, C. Tetrahedron Lett. 2000, 41, 10009-10012.
31. (e) Briot, E.; Piquemal, J.-Y.; Vennat, M.; Brégeault, J.-M.; Chottard, G.; Manoli, J.-M. J. Mater. Chem. 2000, 10, 953-958.
32. (f) Ichihara, J. Tetrahedron Lett. 2001, 42, 695-697.
33. Bergbreiter and co-workers reported excellent homogeneous catalysts prepared from poly(N-isopropylacrylamide) copolymers as soluble and thermoresponsive polymers: (a) Bergbreiter, D. E. Catal. Today 1998, 42, 389-397.
34. (b) Bergbreiter, D. E.; Liu, Y.-S.; Osburn, P. L. J. Am. Chem. Soc. 1998, 120, 4250-4251.
35. (c) Bergbreiter, D. E.; Case, B. L.; Liu, Y.-S.; Caraway, J. W. Macromolecules 1998, 31, 6053-6062.
36. Examples on polymer-protected nanoparticles: (d) Chen, C.-W.; Akashi, M. Polym. Adv. Technol. 1999, 10, 127-133.
37. (e) Chen, C-W.; Chen, M.-Q.; Serizawa,T.; Akashi, M. Chem. Commun. 1998, 831-832.
38. 3 was effective for the enhancement of selectivity of epoxidation. See ref 7a.
39. 40 in place of 3, 8b was not obtained.
40. It was reported that pH control in aqueous media was important for tungsten-catalyzed epoxidation; see refs 6d,e and 7b.
41. 2O is ca. 40-60 (purchased from Wako Pure Chemical Industries, Ltd., Japan) and complete evaporation of water from 3 should be difficult.