Vanadium-catalyzed asymmetric epoxidation of homoallylic alcohols

Journal of the American Chemical Society

Volumn 129, Issue 2, 2007, Pages 286-287

  Zhang, Wei ^a   Yamamoto, Hisashi ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; HOMOALLYLIC ALCOHOL DERIVATIVE; UNCLASSIFIED DRUG; VANADIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; COMPLEX FORMATION; ENANTIOSELECTIVITY; EPOXIDATION; REACTION ANALYSIS;

ALCOHOLS; ALLYL COMPOUNDS; CATALYSIS; EPOXY COMPOUNDS; LIGANDS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; VANADIUM;

EID: 33846214050     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja067495y     Document Type: Article

References (34)

1. For recent reviews, see: (a) Katsuki, T. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin. 1999; Vol. 2, p 621.
2. (b) Katsuki, T.; Ojima, I. Org. React. 1996, 48, 1.
3. (c) Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 5.
4. (d) Adam, W.; Sana-Möller, C. R.; Ganeshpure, P. A. Chem. Rev. 2001, 101, 3499.
5. (e) Adam, W.; Malisch, W.; Roschmann, K. J.; Saha-Möller, C. R.; Schenk, W. A. J. Organomet. Chem. 2002, 661, 3.
6. (f) Lattanzi, A.; Scettri, A. J. Organomet. Chem. 2006, 691, 2072.
7. (g) Shi, Y. Acc. Chem. Res. 2004, 37, 488.
8. (h) Shi, Y.; Frohn, M. Synthesis 2000, 14, 1979.
9. (a) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974.
10. (b) Rossiter, B. E.; Sharpless, K. B. J. Org. Chem. 1984, 49, 3707.
11. (c) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
12. For Zr-catalyzed epoxidation of homoallylic alcohols, see: (a) Ikegami, S.; Katsuki, T.; Yamaguchi, M. Chem. Lett. 1987, 83.
13. (b) Okashi, T.; Murai, N.; Onaka, M. Org. Lett. 2003, 5, 85.
14. Makita, N.; Hoshino, Y.; Yamamoto, H. Angew. Chem., Int. Ed. 2003, 42, 941.
15. For a related epoxidation of allylic alcohols, see: (a) Murase, Y.; Hoshino, Y.; Oishi, M.; Yamamoto, H. J. Org. Chem. 1999, 64, 338.
16. (b) Hoshino, Y.; Murase, N.; Oishi, M.; Yamamoto, H. Bull. Chem. Soc. Jpn. 2000, 73, 1653.
17. (c) Hoshino, Y.; Yamamoto, H. J. Am. Chem. Soc. 2000, 122, 10452.
18. Zhang, W.; Basak, A.; Kosugi, Y.; Hoshino, Y.; Yamamoto, H. Angew. Chem., Int. Ed. 2005, 44, 4389.
19. For recent reports on chiral vanadium catalyst for epoxidation, see: (a) Bryliakov, K. P.; Talsi, E. P. Kinet. Katal 2003, 44, 334.
20. (b) Bolm, C.; Kuhn, T. Synlett 2000, 899.
21. (c) Traber, B.; Jung, Y. G.; Park, T. K.; Hong, J. I. Bull. Korean Chem. Soc. 2001, 22, 547.
22. (d) Wu, H. L.; Uang, B. J. Tetrahedron: Asymmetry 2002, 13, 2625.
23. (e) Bourhani, Z.; Malkov, A. V. Chem. Commun. 2005, 4592.
24. (f) Lattanzi, A.; Piccirillo, S.; Scettri, A. Eur. J. Org. Chem. 2005, 1669.
25. For recent reviews on vanadium, see: (a) Hirao, T. Chem. Rev. 1997, 97, 2707.
26. (b) Bolm, C. Coord. Chem. Rev. 2003, 237, 245.
27. (c) Ligtenbarg, A. G.; Hage, R.; Feringa, B. L. Coord. Chem. Rev. 2003, 237, 89.
28. For mechanistic study on vanadium-hydroxamic acid oxidation, see: (a) Bryliakov, K. P.; Talsi, E. P. Kinet. Katal. 2003, 44, 334.
29. (b) Bryliakov, K. P.; Talsi, E. P.; Kuehn, T.; Bolm, C. New J. Chem. 2003, 27, 609.
30. (c) Adam, W.; Beck, A. K.; Pichota, A.; Saha-Möller, C. R.; Seebach, D.; Vogl, N.; Zhang, R. Tetrahedron: Asymmetry 2003, 14, 1355. (Diagram presented)
31. (a) Enantiomeric excess values were determined by chiral GC analysis, and the detailed information is provided in Supporting Information. The absolute configurations of 4a and 4b were determined as (R) and (R), respectively, by comparison of retention times (GC analysis) of the absolute configuration known compounds (9a, 9b), which were prepared by the following reported sequence: Ehrlich, G.; Kalesse, M. Synlett 2005, 4, 655. Detailed information is provided in Supporting information.
32. (b) For the stereoselective epoxidation of homoallylic alcohols, see: Mihelich, E. D.; Daniels, K.; Eickhoff, D. J. J. Am. Chem. Soc. 1981, 103, 7690.
33. Kende, A. S.; Toder, B. H. J. Org. Chem. 1982, 47, 167.
34. To explain these enantioselectivities, as well as those of kinetic resolutions, we proposed a possible model of the asymmetric epoxidation of homoallylic alcohol catalyzed by the complex of vanadium and ligand 1d, which is provided in the Supporting Information.