Highly effective transition structure designed catalyst for the enantio-and position-selective dihydroxylation of polyisoprenoids

Organic Letters

Volumn 3, Issue 20, 2001, Pages 3211-3214

  Corey, E J ^a   Zhang, Junhu ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CINCHONA ALKALOID; DITERPENE; OSMIUM TETRAOXIDE; PROPYLENE;

ARTICLE; CHEMISTRY; HYDROXYLATION; STEREOISOMERISM; SYNTHESIS;

ALKENES; CINCHONA ALKALOIDS; DITERPENES; HYDROXYLATION; OSMIUM TETROXIDE; STEREOISOMERISM;

EID: 0035807539     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016577i     Document Type: Article

References (40)

1. For a review of the catalytic asymmetric dihydroxylation of olefins, see: Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
2. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768.
3. Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 11038.
4. (a) Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1993, 115, 12579.
5. (b) Corey, E. J.; Noe, M. C.; Sarshar, S. Tetrahedron Lett. 1994, 35, 2861.
6. Corey, E. J.; Noe, M. C.; Grogan, M. J. Tetrahedron Lett. 1994, 35, 6427.
7. Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 319.
8. (e) Corey, E. J.; Noe, M. C.; Sarshar, S. J. Am. Chem. Soc. 1993, 115, 3828.
9. (a) Corey, E. J.; Guzman-Perez, A.; Noe, M. C. J. Am. Chem. Soc. 1995, 117, 10805.
10. (b) Corey, E. J.; Guzman-Perez, A.; Noe, M. C. Tetrahedron Lett. 1995, 36, 3481.
11. Corey, E. J.; Noe, M. C.; Ting, A. Tetrahedron Lett. 1996, 37, 1735.
12. Corey, E. J.; Noe, M. C.; Lin, S. Tetrahedron Lett. 1995, 36, 8741.
13. (e) Corey, E. J.; Noe, M. C.; Guzman-Perez, A. J. Am. Chem. Soc. 1995, 117, 10817.
14. (a) Corey, E. J.; Noe, M. C.; Grogan, M. J. Tetrahedron Lett. 1996, 37, 4899. See also:
15. (b) DelMonte, A. J.; Haller, J.; Houk, K. N.; Sharpless, K. B.; Singleton, D. A.; Strassner, T.; Thomas, A. A. J. Am. Chem. Soc. 1997, 119, 9907.
16. Corey, E. J.; Sarshar, S.; Azimioara, M. D.; Newbold, R. C.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 7851.
17. (a) Dapprich, S.; Ujaque, G.; Maserus, F.; Lledós, A.; Musaev, D. G.; Morokuma, K. J. Am. Chem. Soc. 1996, 118, 11660.
18. (b) Pidun, U.; Boehme, C.; Frenking, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 2817.
19. Torrent, M.; Deng, L.; Duran, M.; Sola, M.; Ziegler, T. Organometallics 1997, 16, 13.
20. Hentges, S. G.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 4263.
21. (a) Norrby, P.-O.; Kolb, H. C.; Sharpless, K. B. Organometallics 1994, 13, 344.
22. (b) Norrby, P.-O.; Kolb, H. C.; Sharpless, K. B. J. Am. Chem. Soc. 1994, 116, 8470.
23. Becker, H.; Ho, P. T.; Kolb, H. C.; Loren, S.; Norrby, P.-O.; Sharpless, K. B. Tetrahedron Lett. 1994, 35, 7315.
24. Norrby, P.-O.; Becker, H.; Sharpless, K. B. J. Am. Chem. Soc. 1996, 118, 35.
25. (e) Sharpless, K. B.; Teranishi, A. Y.; Bäckvall, J.-E. J. Am. Chem. Soc. 1977, 99, 3120.
26. (f) Jørgensen, K. A.; Schiøtt, B. Chem. Rev. 1990, 90, 1483.
27. Chem. Eng. News. 1997, 75 (Nov 3), 23.
28. Nelson, D. W.; Gypser, A.; Ho, P. T.; Kolb, H. C.; Kondo, T.; Kwong, H.-L.; McGrath, D. V.; Rubin, A. E.; Norrby, P.-O.; Gable, K. P.; Sharpless, K. B. J. Am. Chem. Soc. 1997, 119, 1840.
29. Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986.
30. Hill, J. H. M.; Ehrlich, J. H. J. Org. Chem. 1971, 36, 3248.
31. Heidelberger, M.; Jacobs, W. A. J. Am. Chem. Soc. 1919, 41, 817.
32. Sasaki, H.; Irie, R.; Hamada, T.; Suzuki, K.; Katsuki, T. Tetrahedron 1994, 50, 11827.
33. Wolfe, J. P.; Åhman, J.; Sadighi, J. P.; Singer, R. A.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6367.
34. Crispino, G. A.; Sharpless, K. B. Tetrahedron Lett. 1992, 33, 4273.
35. 1H NMR analysis of the mono-(S)-MTPA (Mosher) ester using racemic mono Mosher ester as standard.
36. 2Cl-py, then base) to the corresponding (S)-epoxides, which are useful for the enantioselective synthesis of many polycyclic natural products. See, for example: (a) Huang, A. X.; Xiong, Z.; Corey, E. J. J. Am. Chem. Soc. 1999, 121, 9999.
37. (b) Corey, E. J.; Lin, S. J. Am. Chem. Soc. 1996, 118, 8765.
38. Corey, E. J.; Luo, G.; Lin, S. J. Am. Chem. Soc. 1997, 119, 9927.
39. Corey, E. J.; Lee, J. J. Am. Chem. Soc. 1993, 115, 8873.
40. (e) Corey, E. J.; Lee, J.; Liu, D. R. Tetrahedron Lett. 1994, 35, 9149.