Enzymatic-like mediated olefins epoxidation by molecular oxygen under mild conditions

Tetrahedron Letters

Volumn 48, Issue 15, 2007, Pages 2691-2695

  Zhou, Xian Tai ^a   Ji, Hong Bing ^a   Xu, Jian Chang ^a   Pei, Li Xia ^a   Wang, Le Fu ^a   Yao, Xing Dong ^b  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

^b GUANGXI UNIVERSITY FOR NATIONALITIES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; OXYGEN; TETRAPHENYLPORPHYRIN DERIVATIVE;

ARTICLE; ATMOSPHERIC PRESSURE; CATALYSIS; CATALYST; ENVIRONMENTAL TEMPERATURE; ENZYME MECHANISM; EPOXIDATION; REACTION ANALYSIS;

EID: 33947128629     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.02.066     Document Type: Article

References (34)

1. Meunier B. Biomimetic Oxidations Mediated by Metal Complexes (2000), Imperial College Press, London
2. Groves J.T., and Nemo T.E. J. Am. Chem. Soc. 105 (1983) 5786-5791
3. Dolphin D., Traylor T.G., and Xie L.Y. Acc. Chem. Res. 30 (1997) 251-259
4. do Nascimento E., Silva G.D., Caetano F.A., Fernandez M.A.M., da Silva D.C., de Carvalho M.E.M.D., Pernaut J.M., Reboucas J.S., and Idemori Y.M. J. Inorg. Biochem. 99 (2005) 1193-1204
5. Gross Z., and Ini S. J. Org. Chem. 62 (1997) 5514-5521
6. de Sousa A.N., de Carvalho M.E.M.D., and Idemori Y.M. J. Mol. Catal. A 169 (2001) 1-10
7. Li Z., Xia C.G., and Ji M. Appl. Catal., A 252 (2003) 17-21
8. Campestrini S., and Tonellato U. J. Mol. Catal. A 171 (2001) 37-42
9. Gonsalves A.M.D.R., and Serra A.C. J. Porphyrins Phthalocyanines 4 (2000) 598-603
10. Nam W., Oh S.-Y., Sun Y.J., Kim J., Kim W.-K., Woo S.K., and Shin W. J. Org. Chem. 68 (2003) 7903-7906
11. Haber J., Iwanejko R., Poltowicz J., Battioni P., and Mansuy D. J. Mol. Catal. A 152 (2000) 111-115
12. Haber J., Iwanejko R., Poltowicz J., Battioni P., and Mansuy D. J. Mol. Catal. A 152 (2000) 117-120
13. Mohajer D., and Rezaeifard A. Tetrahedron Lett. 43 (2002) 1881-1884
14. Mohajer D., Karimipour G., and Bagherzadeh M. New J. Chem. 28 (2004) 740-747
15. Lyons J.E., and Ellis P.E. J. Catal. 155 (1995) 59-73
16. Haber J., Matachowski L., Pamin K., and Poltowicz J. J. Mol. Catal. A 162 (2000) 105-109
17. Guo C.C., Chu M.F., Liu Q., Liu Y., Guo D.C., and Liu X.Q. Appl. Catal., A 246 (2003) 303-309
18. Haber J., Matachowski L., Pamin K., and Poltowicz J. J. Mol. Catal. A 198 (2003) 215-221
19. Ellis S., and Kozhevnikov I.V. J. Mol. Catal. A 187 (2002) 227-235
20. Haber J., Mlodnicka T., and Poltowicz J. J. Mol. Catal. 54 (1989) 451-461
21. Mandal A.K., and Iqbal J. Tetrahedron 53 (1997) 7641-7648
22. Yuan Y., Ji H.B., Chen Y.X., Han Y., Song X.F., She Y.B., and Zhong R.G. Org. Process Res. Dev. 8 (2004) 418-420
23. Song X.F., She Y.B., Ji H.B., and Zhang Y.H. Org. Process Res. Dev. 9 (2005) 297-301
24. meso-Tetraphenylporphyrin (TPP) was prepared according to the known procedure, see:. Alder A.D., Longo F.R., Finarelli J.D., Goldmacher J., Assour J., and Korsakoff L. J. Org. Chem. 32 (1967) 476
25. -1.
26. -7 mmol) and 0.8 mmol naphthalene (inert internal standard) at room temperature. The consumption of the starting olefins and formation of oxidized products were monitored by GC (Shimadzu GC14C) and GC-MS (Shimadzu GCMS-QP5050A).
27. Qi J.Y., Qiu L.Q., Lam K.H., Yip C.W., Zhou Z.Y., and Chan A.S.C. Chem. Commun. (2003) 1058-1059
28. Nam W., Baek S.J., Lee K.A., Ahn B.T., Muller J.G., Burrows C.J., and Valentine J.S. Inorg. Chem. 35 (1996) 6632-6633
29. Nam W., Kim H.J., Kim S.H., Ho R.Y.N., and Valentine J.S. Inorg. Chem. 35 (1996) 1045-1049
30. Ravikumar K.S., Barbier F., Begue J.P., and Delpon D.B. Tetrahedron 54 (1998) 7457-7464
31. -8 mmol) were added in the presence of molecular oxygen at room temperature. The crude products were purified via column chromatography (silica gel, cyclohexane as eluting agent). After removing solvent under reduced pressure, the pure cyclohexene oxide (1.76 g) was obtained with the yield of 90%.
32. Wang L.Z., She Y.B., Zhong R.G., Ji H.B., Zhang Y.H., and Song X.F. Org. Process Res. Dev. 10 (2006) 757-761
33. Arasasingham R.D., He G.X., and Bruice T.C. J. Am. Chem. Soc. 115 (1993) 7985-7991
34. Chan W.K., Wong M.K., and Che C.M. J. Org. Chem. 70 (2005) 4226-4232