A facile method for the epoxidation of cyclic enone catalyzed by tert-BuNH2 with 30% hydrogen peroxide as oxidant

Chinese Journal of Chemistry

Volumn 24, Issue 10, 2006, Pages 1480-1482

  Ouyang, Xiao Yue ^a   Jiang, Huan Feng ^b   Huang, Jing Mei ^b  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

, unsaturated ketone; Amine; Catalysis; Epoxidation; Hydrogen peroxide

Indexed keywords

EID: 33751003489     PISSN: 1001604X     EISSN: None     Source Type: Journal    
DOI: 10.1002/cjoc.200690280     Document Type: Article

References (23)

1. (a) Ho, T. L.; Liu, S. H. Synth. Commun. 1983, 13, 685.
2. (b) Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737.
3. (c) Rao, A. S.; Paknikar, S. K.; Kirtane, J. J. Tetrahedron Lett. 1983, 39, 2323.
4. (d) Smith, G. J. Synthesis 1984, 629.
5. (e) Kotsuki, H.; Kataoka, M.; Nishizawa, H. Tetrahedron Lett. 1993, 34, 4031.
6. (f) Alcaraz, L.; Harnett, J. J.; Mioskowski, C.; Martel, J. P.; Gall, T. L.; Shin, D. S.; Falck, J. R. Tetrahedron Lett. 1994, 35, 5449.
7. (g) Ho, T. L.; Liu, S. L.; SCM Glidco Organics Corp., US 4 359 586, 1981 [Chem. Abstr. 1983, 98, 71548].
8. (a) Lane, B. S.; Burgess, K. Chem. Rev. 2003, 103, 2457.
9. (b) Grigoropoulou, G.; Clark, J. H.; Elings, J. A. Green Chem. 2003, 5, 1.
10. (a) Kim, Y. H.; Hwang, J. P.; Yang, S. G. Tetrahedron Lett. 1997, 38, 3009.
11. (b) Fringuelli, G. F. F.; Pizzo, F.; Vaccaro, L. Green Chem, 2003, 5, 425.
12. (a) Cativiela, C.; Figueras, F.; Fraile, J. M.; Garcia, J. I. Tetrahedron Lett. 1995, 36, 4125.
13. (b) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Org. Chem. 2000. 65, 6897.
14. For recent review on metal-catalyzed epoxidation with hydrogen peroxide, see: (a) Lane, B. S.; Burgess, K. Chem. Rev. 2003, 103, 2457.
15. (b) Murphy, A.; Dubois, G.; Stack, T. D. P. J. Am. Chem. Soc. 2003, 125, 5250.
16. 2, see: (a) Adamo, M. F. A.; Aggarwal, V. K.; Sage, M. A. J. Am. Chem. Soc. 2000, 122, 8317.
17. (b) Aggarwal, V. K.; Lopin, C.; Sandrinelli, F. J. Am. Chem. Soc. 2003, 125, 7596.
18. (c) Ho, C. U.; Chen, Y. C.; Wong, M. K.; Yang, D. J. Org. Chem. 2005, 70, 898.
19. Other examples in epoxidation of α,β-unsaturated compounds in environmentally friendly ways see: (a) Pillai, U. R.; Sahle-Demessie, E. Appl. Catal., A 2004, 69.
20. (b) Fioroni, G.; Fringuelli, F.; Pizzo, F.; Vaccaro, L. Green Chem. 2003, 5, 425.
21. (c) Wang, B.; Kang, Y.-R.; Yang, L.-M.; Suo, J.-S. J. Mol. Catal. A: Chem. 2003, 203, 29.
22. (d) Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623.
23. (e) Bortolini, O.; Campestrini, S.; Conte, V.; Fantin, G.; Fogagnolo, M.; Maieti, S. Eur. J. Org. Chem. 2003, 4804.