Models for stereoselective additions to chiral allylic ethers: Osmium tetroxide bis-hydroxylations

Journal of the American Chemical Society

Volumn 119, Issue 34, 1997, Pages 8031-8034

  Haller, Jan ^a   Strassner, Thomas ^a   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALLYL COMPOUND; OSMIUM TETRAOXIDE;

ARTICLE; CALCULATION; CHEMICAL MODIFICATION; COMPUTER ANALYSIS; CONFORMATION; DENSITY; HYDROXYLATION; STEREOCHEMISTRY;

EID: 0030768660     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971342g     Document Type: Article

References (30)

1. Hofmann, K. A. Chem. Ber. 1912, 45, 3329-3336.
2. Criegee, R. Justus Liebigs Ann. Chem. 1936, 522, 75-96.
3. Review: Schröder, M. Chem. Rev. (Washington, D.C.) 1980, 80, 187-213.
4. (a) Sharpless, K. B.; Akashi, K. J. Am. Chem. Soc. 1976, 98, 1986-1987.
5. (b) Minato, M.; Yamamoto, K.; Tsuji, J. J. Org. Chem. 1990, 55, 766-768.
6. Review: Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. (Washington, D.C.) 1994, 94, 2483-2547.
7. Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron 1984, 40, 2247-2255.
8. Evans, D. A.; Kaldor, S. W. J. Org. Chem. 1990, 55, 1698-1700.
9. Stork, G.; Kahn, M. Tetrahedron Lett. 1983, 24, 3951-3954.
10. Houk, K. N.; Moses, S. R.; Wu, Y.-D.; Rondan, N, G.; Jäger, V.; Schohe, R.; Fronczek, F. R. J. Am. Chem. Soc. 1984, 106, 3880-3882.
11. Vedejs, E.; McClure, C. K. J. Am. Chem. Soc. 1986, 108, 1094-1096.
12. Corey, E. J.; Jardine, P. D.; Virgil, S.; Yuen, P.-W.; Connell, R. D. J. Am. Chem. Soc. 1989, 111, 9243-9244. Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 11038-11053.
13. Corey, E. J.; Jardine, P. D.; Virgil, S.; Yuen, P.-W.; Connell, R. D. J. Am. Chem. Soc. 1989, 111, 9243-9244. Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 11038-11053.
14. (a) Hentges, S. G.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 4263-4265.
15. (b) Sharpless, K. B.; Teranishi, A. Y.; Bäckwall, J.-E. J. Am. Chem. Soc. 1977, 99, 3120-3128.
16. (c) Nelson, D. W.; Gypser, A.; Ho, P. T.; Kolb, H. C.; Kondo, T.; Kwong, H.-L.; McGrath, D. V.; Rubin, A. E.; Norbby, P.-O.; Gable, K. P.; Sharpless, K. B. J. Am. Chem. Soc. 1977, 119, 1840-1858.
17. Göbel, T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1993, 32, 1329-1331.
18. 15
19. (b) Pidun, E.; Boehme, C.; Frenking, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 2817-2820.
20. (c) Dapprich, S.; Ujaque, G.; Maseras, F.; Lledós, A.; Musaev, D. G.; Morokuma, K. J. Am. Chem Soc. 1996, 118, 11660-11661.
21. (d) Torrent, M.; Deng, L.; Duran, M.; Sola, M.; Ziegler, T. Organometallics 1997, 16, 13-19.
22. (a) Corey, E. J.; Noe, M. C.; Grogan, M. J. Tetrahedron Lett. 1996, 37, 4899-4902.
23. (b) Unpublished results in collaboration with D. A. Singleton.
24. Gaussian 94 (Revision C.2): M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, and J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1995.
25. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283, 299-310.
26. (a) Rondan, N. G.; Paddon-Row, M. N.; Caramella, P.; Mareda, J.; Mueller, P. H.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 4974-4976.
27. (b) Paddon-Row, M. N.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 7162-7166.
28. (c) Houk, K. N.; Paddon-Row, M. N.; Rondan, N. G.; Wu, Y.-D.; Brown, F. K.; Spellmeyer, D. C.; Metz, J. T.; Li, Y.; Loncharich, R. J. Science 1986, 231, 1108-1117.
29. (d) Martinelli, M. J.; Peterson, B. C.; Khau, V. V.; Hutchison, D. R.; Leanna, M. R.; Audia, J. E.; Droste, J. J.; Wu, Y.-D.; Houk, K. N. J. Org. Chem. 1994, 59, 2204-2210.
30. The dihedral angle d(HOCC) was fixed at 180° to prevent a hydrogen bond to the oxygen atom of the osmium tetroxide. Allowing the hydrogen bond lowers the energy of the transition structure by 3.0 kcal/ mol.