High enantioselectivities in an (E)-alkene epoxidation by catalytically active chromium salen complexes. Insight into the catalytic cycle

Organic Letters

Volumn 3, Issue 5, 2001, Pages 663-666

  Daly, Adrian M ^a   Renehan, Marie F ^a   Gilheany, Declan G ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0001739256     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0069406     Document Type: Article

References (34)

1. Dalton, C. T.; Ryan, K. M.; Wall, V. M.; Bousquet, C.; Gilheany, D. G. Top. Catal. 1998, 5, 71-90.
2. (a) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed: Wiley-VCH: New York, 2000; Chapter 6A.
3. (b) Jacobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer, New York, 1999; Chapter 18.2, pp 649-677.
4. (c) Katsuki, T. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed; Wiley-VCH: New York, 2000; Chapter 6B.
5. (d) Wang, Z.; Tu, Y.; Frohn, M.; Shi, Y. J. Org. Chem. 1997, 62, 2328-2329.
6. Bousquet, C., Gilheany, D. G. Tetrahedron Lett. 1995, 36, 7739-7742.
7. Dalton, C. T.; Ryan, K. M.; Coyne, E. J.; Wall, V. M.; Bousquet, C.; Gilheany, D. G. Abstracts of Papers; 211th National Meeting of the American Chemical Society, New Orleans, LA.; American Chemical Society: Washington, DC, 1996; ORGN 161-165.
8. Ryan, K. M.; Bousquet, C.; Gilheany, D. G. Tetrahedron Lett. 1999, 40, 3613-3616.
9. Daly, A. M.; Dalton, C. T.; Renehan, M. F.; Gilheany, D. G. Tetrahedron Lett. 1999, 40, 3617-3620.
10. Samsel, E. G.; Srinivasan, K.; Kochi, J. K. J. Am. Chem. Soc. 1985, 107, 7606-7617.
11. A ruthenium salen complex has recently been shown to catalyse the epoxidation of E,Z and terminal alkenes in 80-90% ee: Takeda, T.; Irie, R.; Shinoda, Y.; Katsuki, T. SynLett 1999, 1157-1159.
12. Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 263, 1404-1411. Groves, J. T.; Nemo, T. E. J. Am Chem. Soc. 1983, 105, 5786-5791.
13. Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 263, 1404-1411. Groves, J. T.; Nemo, T. E. J. Am Chem. Soc. 1983, 105, 5786-5791.
14. Houk, K. N.; DeMello, N. C.; Condroski, K.; Fennen, J.; Kasuga, T. Origins of Stereoselecivity in Jacobsen Epoxidations. Electronic Conference on Heterocyclic Chemistry, ECHET96, 24/6-22/7 1996; Rzepa, H. S., Snyder, J. P., Leach, C., Eds.; London; http://www.ch.ic.ac.uk/ectoc/echet96/.
15. Houk, K. N.; DeMello, N. C.; Condroski, K.; Fennen, J.; Kasuga, T. Origins of Stereoselecivity in Jacobsen Epoxidations. Electronic Conference on Heterocyclic Chemistry, ECHET96, 24/6-22/7 1996; Rzepa, H. S., Snyder, J. P., Leach, C., Eds.; London; http://www.ch.ic.ac.uk/ectoc/echet96/.
16. Hamada, T.; Fukuda, T.; Imanishi, H.; Katsuki, T. Tetrahedron 1996, 52, 515-530. Ito, Y. N.; Katsuki, T. Tetrahedron Lett. 1998, 39, 4325. Irie, R.; Hashihayata, T.; Katsuki, T.; Akita, M.; Moro-oka, Y. Chem. Lett. 1998, 1041-1042.
17. Hamada, T.; Fukuda, T.; Imanishi, H.; Katsuki, T. Tetrahedron 1996, 52, 515-530. Ito, Y. N.; Katsuki, T. Tetrahedron Lett. 1998, 39, 4325. Irie, R.; Hashihayata, T.; Katsuki, T.; Akita, M.; Moro-oka, Y. Chem. Lett. 1998, 1041-1042.
18. Hamada, T.; Fukuda, T.; Imanishi, H.; Katsuki, T. Tetrahedron 1996, 52, 515-530. Ito, Y. N.; Katsuki, T. Tetrahedron Lett. 1998, 39, 4325. Irie, R.; Hashihayata, T.; Katsuki, T.; Akita, M.; Moro-oka, Y. Chem. Lett. 1998, 1041-1042.
19. Very recently the use of a Mn(salen) complex to epoxidize E-alkenes in good ee was reported: Nishikori, H.; Ohta, C.; Katsuki, T. SynLett 2000, 1557-1560.
20. Murphy, S. T., Zou, C.; Miers, J. B.; Ballew, R.; Dlott, D.; Schuster, G. B. J. Phys. Chem. 1993, 97, 13152-13157.
21. Groves, J. T.; Kruper, W. J.; Haushalter, R. C. J. Am. Chem. Soc. 1980, 102, 6377-6380.
22. (a) Pietikäinen, P. Tetrahedron 2000, 56, 417-424.
23. (b) Irie, R.; Hosoya, N.; Katsuki, T. Synlett 1994, 255-256.
24. (c) Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063-7064.
25. Katsuki, T.; Imanishi, H. Tetrahedron Lett. 1997, 38, 251-254.
26. Plattner, D. A.; Feichtinger, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 1718-1719. Plattner, D. A.; Feichtinger, D.; El-Bahraoui, J.; Wiest, O. Int. J. Mass. Spectrom. 2000, 195/196, 351-362. Feichtinger, D.; Planner, D. A. J. Chem. Soc., Perkin Trans. 2 2000, 1023-1028.
27. Plattner, D. A.; Feichtinger, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 1718-1719. Plattner, D. A.; Feichtinger, D.; El-Bahraoui, J.; Wiest, O. Int. J. Mass. Spectrom. 2000, 195/196, 351-362. Feichtinger, D.; Planner, D. A. J. Chem. Soc., Perkin Trans. 2 2000, 1023-1028.
28. Plattner, D. A.; Feichtinger, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 1718-1719. Plattner, D. A.; Feichtinger, D.; El-Bahraoui, J.; Wiest, O. Int. J. Mass. Spectrom. 2000, 195/196, 351-362. Feichtinger, D.; Planner, D. A. J. Chem. Soc., Perkin Trans. 2 2000, 1023-1028.
29. Collman, J. P.; Chien, A. S.; Eberspacher, T. A.; Brauman, J. I. J. Am. Chem. Soc. 2000, 122, 11098-11100.
30. Yang, Y.; Diederich, F.; Valentine, J. S. J. Am. Chem. Soc. 1991, 113, 7195-7205.
31. 7
32. Woo, L. K. Chem. Rev. 1993, 93, 1125. Parkin, G. Prog. Inorg. Chem. 1998, 47, 1.
33. Woo, L. K. Chem. Rev. 1993, 93, 1125. Parkin, G. Prog. Inorg. Chem. 1998, 47, 1.
34. Srinivasan, K.; Michaud, P.; Kochi, J. K. J. Am. Chem. Soc. 1986, 108, 2309-2320.