A novel and highly efficient asymmetric synthesis of epoxides via chiral telluronium ylides

Synthesis

Volumn , Issue 17, 2005, Pages 2857-2860

  Ou, Wen Hua ^a   Huang, Zhi Zhen ^a  

^a NANJING UNIVERSITY   (China)

Author keywords

Asymmetric synthesis; Chiral epoxide; Enantioselectivity; One pot reaction; Telluronium ylide

Indexed keywords

REACTION KINETICS; SYNTHESIS (CHEMICAL);

ASYMMETRIC SYNTHESIS; CHIRAL EPOXIDES; ENANTIOSELECTIVITY; ONE-POT REACTIOJN; TELLURONIUM YLIDE;

TELLURIUM COMPOUNDS;

ALDEHYDE; EPOXIDE; POTASSIUM; SELENIUM DERIVATIVE; SULFONIUM DERIVATIVE; TELLURIUM DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; EPOXIDATION; ROOM TEMPERATURE; SYNTHESIS;

EID: 27944487487     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-872169     Document Type: Article

References (25)

1. (a) Hatakeyama, S.; Ochi, N.; Takano, S. Chem. Pharm. Bull. 1993, 41, 1358.
2. (b) Jerina, D. M.; Daloy, J. W. Science (Washington, D.C.) 1974, 185, 573.
3. (c) Becker, A. R.; Janusz, J. M.; Bruice, T. C. J. Am. Chem. Soc. 1979, 101, 5679.
4. (a) Hudlicky, T.; Tian, X.; Königsberger, K.; Rouden, J. J. Org. Chem. 1994, 59, 4037.
5. (b) Shao, H.; Zhu, Q.; Goodman, M. J. Org. Chem. 1995, 60, 790.
6. (c) Shoulié, J.; Boyer, T.; Lallemand, J. Y. Tetrahedron: Asymmetry 1995, 6, 625.
7. (a) Bartók, M.; Lang, K. L. The Chemistry of Functional Groups; Patai, S., Ed.; Wiley: New York, 1980, Supplement E, 609-681.
8. (b) Gorzynski, S. Synthesis 1984, 629.
9. (c) Rao, A. K.; Paknikar, S. K.; Kirtance, J. G. Tetrahedron 1983, 39, 2323.
10. Li, A. H.; Dai, L. X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341.
11. (a) Zanardi, J.; Leriverend, C.; Aubert, D.; Julienne, K.; Metzner, P. J. Org. Chem. 2001, 66, 5620.
12. (b) Breau, L.; Ogilive, W.-W.; Durst, T. Tetrahedron Lett. 1990, 31, 35.
13. (c) Zanardi, J.; Lamazure, D.; Miniere, S.; Reboul, V.; Metzner, P. J. Org. Chem. 2002, 67, 9083.
14. (d) Julienne, K.; Metzner, P.; Henryon, V. J. Chem. Soc., Perkin Trans. 1 1999, 731.
15. (e) Julienne, K.; Metzner, P.; Julienne, K.; Metzner, P.; Henryon, V.; Greiner, A. J. Org. Chem. 1998, 63, 4532.
16. Takada, H.; Metzner, P.; Philouze, C. Chem. Commun. 2001, 2350.
17. Huang, Y.-Z.; Tang, Y.; Zhou, Z.-L. Tetrahedron 1998, 54, 1667.
18. (a) Lieser, J.-K. Synth. Commun. 1983, 13, 765.
19. (b) Liao, W.-W.; Li, K.; Tang, Y. J. Am. Chem. Soc. 2003, 43, 13031.
20. (a) Endo, T.; Kanda, N. J. Polym. Sci., Polym. Chem. Ed. 1985, 23, 1931.
21. (b) Auge, J.; David, S. Tetrahedron Lett. 1983, 24, 4009.
22. (a) Li, A.-H.; Dai, L.-X.; Hou, X.-L.; Huang, Y.-Z.; Li, F.-W. J. Org. Chem. 1996, 61, 489.
23. (b) Oudeyer, S.; Léonel, E.; Paugam, J. P.; Nédélec, J.-Y. Synthesis 2004, 389.
24. (c) Aggarwal, V. K.; Alonso, E.; Bae, L; Hynd, G.; Lydon, K. M.; Palmer, M. J.; Patel, M.; Porcelloni, M.; Richardson, J.; Stenson, R. A.; Studley, J. R.; Vasse, J.-L.; Winn, C. L. J. Am. Chem. Soc. 2003, 125, 10926.
25. (d) Futamura, S.; Kusunose, S. J. Chem. Soc., Perkin Trans. 1 1984, 15.