Homogeneous dihydroxylation of olefins catalyzed by a recyclable OsO42 - core dendrimer

Tetrahedron Letters

Volumn 51, Issue 5, 2010, Pages 808-810

  Fujita, Ken ichi ^a   Ainoya, Taku ^b   Tsuchimoto, Teruhisa ^b   Yasuda, Hiroyuki ^a  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^b MEIJI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; DENDRIMER; OSMATE; OSMIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; DIHYDROXYLATION;

EID: 73049108000     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.11.126     Document Type: Article

References (51)

1. Schröder M. Chem. Rev. 80 (1980) 187-213
2. Hammond, C. R. In CRC Handbook of Chemistry and Physics, 81st ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, FL, 2000, p. 4.
3. Leadbeater N.E., and Marco M. Chem. Rev. 102 (2002) 3217-3274
4. 2 - by ion-exchange technique:. Jun B.-H., Kim J.-H., Park J., Kang H., Lee S.-H., and Lee Y.-S. Synlett (2008) 2313-2316
5. Jiang R., Kuang Y., Sun X., and Zhang S. Acta Chim. Slov. 52 (2005) 467-470
6. Kim K.J., Choi H.Y., Hwang S.H., Park Y.S., Kwueon E.K., Choi D.S., and Song C.E. Chem. Commun. (2005) 3337-3339
7. Choudary B.M., Jyothi K., Kantam M.L., and Sreedhar B. Adv. Synth. Catal. 346 (2004) 45-48
8. Choudary B.M., Chowdari N.S., Jyothi K., and Kantam M.L. J. Am. Chem. Soc. 124 (2002) 5341-5349
9. 4:. Ishida T., Akiyama R., and Kobayashi S. Adv. Synth. Catal. 347 (2005) 1189-1192
10. Ley S.V., Ramarao C., Lee A.-L., Østergaard N., Smith S.C., and Shirley I.M. Org. Lett. 5 (2003) 185-187
11. Nagayama S., Endo M., and Kobayashi S. J. Org. Chem. 63 (1998) 6094-6095
12. Lee B.S., Mahajan S., and Janda K.D. Tetrahedron Lett. 46 (2005) 4491-4493
13. Miao J.H., Yang J.-H., Chen L.-Y., Tu B.-X., Huang M.Y., and Jiang Y.-Y. Polym. Adv. Technol. 15 (2004) 221-224
14. Yang J.W., Han H., Roh E.J., Lee S.-g., and Song C.E. Org. Lett. 4 (2002) 4685-4688
15. Severeyns A., De Vos D.E., Fiermans L., Verpoort F., Grobet P.J., and Jacobs P.A. Angew. Chem., Int. Ed. 40 (2001) 586-589
16. Jiang R., Kuang Y., Sun X., and Zhang S. Tetrahedron: Asymmetry 15 (2004) 743-746
17. Chandrasekhar S., Narsihmulu C., Sultana S.S., and Reddy N.R. Chem. Commun. (2003) 1716-1717
18. Yao Q. Org. Lett. 4 (2002) 2197-2199
19. In: Fréchet J.M.J., and Tomalia D.A. (Eds). Dendrimers and Other Dendritic Polymers (2001), John Wiley & Sons, New York
20. Newkome G.R., Moorefield C.N., and Vogtle F. Dendrimers and Dendrons (2001), Wiley-VCH, Weinheim
21. Chase P.A., Gebbink R.J.M.K., and van Koten G. J. Organomet. Chem. 689 (2004) 4016-4054
22. Fréchet J.M.J. J. Polym. Sci.: Part A: Polym. Chem. 41 (2003) 3713-3725
23. In: Gade L.H. (Ed). Dendrimer Catalyst (2006), Springer-Verlag, Berlin, Heidelberg
24. Méry D., and Astruc D. Coord. Chem. Rev. 250 (2006) 1965-1979
25. Grayson S.M., and Fréchet J.M.J. Chem. Rev. 101 (2001) 3819-3867
26. Astruc D., and Chardac F. Chem. Rev. 101 (2001) 2991-3023
27. Twyman L.J., King A.S.H., and Martin I.K. Chem. Soc. Rev. 31 (2002) 69-82
28. Muraki T., Fujita K., and Kujime M. J. Org. Chem. 72 (2007) 7863-7870
29. Hattori H., Fujita K., Muraki T., and Sakaba A. Tetrahedron Lett. 48 (2007) 6817-6820
30. Fujita K., Muraki T., Hattori H., and Sakakura T. Tetrahedron Lett. 47 (2006) 4831-4843
31. Muraki T., Fujita K., and Terakado D. Synlett (2006) 2646-2648
32. Snelders D.J.M., van Koten G., and Gebbink R.J.M.K. J. Am. Chem. Soc. 131 (2009) 11407-11416
33. Wang Z.-J., Deng G.-J., Li Y., He Y.-M., Tang W.-J., and Fan Q.-H. Org. Lett. 9 (2007) 1243-1246
34. Helms B., Liang C.O., Hawker C.J., and Fréchet J.M.J. Macromolecules 38 (2005) 5411-5415
35. Fujihara T., Obora Y., Tokunaga M., Sato H., and Tsuji Y. Chem. Commun. (2005) 4526-4528
36. Zhang X., Xu H., Dong Z., Wang Y., Liu J., and Shen J. J. Am. Chem. Soc. 126 (2004) 10556-10557
37. Fan Q.-H., Chen Y.-M., Chen X.-M., Jiang D.-Z., Xi F., and Chan A.S.C. Chem. Commun. (2000) 789-790
38. Iwasawa T., Tokunaga M., Obora Y., and Tsuji Y. J. Am. Chem. Soc. 126 (2004) 6554-6555
39. However osmium core dendrimers have been reported previously, their catalytic activity was as low as in the case of heterogeneity:. Tang W.-J., Yang N.-F., Yi B., Deng G.-J., Huang Y.-Y., and Fan Q.-H. Chem. Commun. (2004) 1378-1379
40. Muraki T., Fujita K., Oishi A., and Taguchi Y. Polym. J. 37 (2005) 847-853
41. Tomoyose Y., Jiang D.-L., Jin R.-H., Aida T., Yamashita T., Horie K., Yashima E., and Okamoto Y. Macromolecules 29 (1996) 5236-5238
42. Hawker C.J., and Fréchet J.M.J. J. Am. Chem. Soc. 112 (1990) 7638-7647
43. -1; Anal. Found: C, 59.80; H, 5.62; N, 1.13; Br, 4.79; Os, 4.13.
44. 2O (4:1, v/v) solution (4 mL) of 2(G3) (0.01 mmol) were added olefin (1 mmol) and N-methylmorpholine N-oxide (NMO; 1.2 mmol) successively at room temperature under an argon atmosphere. After stirring the resulting mixture for 0.5-3 h, the dihydroxylation reaction was completed (monitored by TLC or GC). The reaction mixture was evaporated and dissolved in a small amount of acetone. The acetone solution was poured into 6 mL of water to precipitate 2(G3) as a grayish powder. After centrifugal separation, the aqueous solution was decanted, and the recovered 2(G3) was reused for subsequent dihydroxylation reactions.
45. Reviews of the dendritic effect:. Helms B., and Fréchet J.M.J. Adv. Synth. Catal. 348 (2006) 1125-1148
46. Chow H.-F., Leung C.-F., Wang G.-X., and Yang Y.-Y. C.R. Chimie 6 (2003) 735-745
47. Examples of dendritic effect on selectivity:. Benito J.M., de Jesús E., de la Mata F.J., Flores J.C., and Gómez R. Chem. Commun. (2005) 5217-5219
48. Fujita K., Muraki T., Sakurai T., Oishi A., and Taguchi Y. Chem. Lett. 34 (2005) 1180-1181
49. Ribourdouille Y., Engel G.D., Plouet M.R., and Gade L.H. Chem. Commun. (2003) 1228-1229
50. Mizugaki T., Murata M., Ooe M., Ebitani K., and Kaneda K. Chem. Commun. (2002) 52-53
51. Bhyrappa P., Young J.K., Moore J.S., and Suslick K.S. J. Am. Chem. Soc. 118 (1996) 5708-5711