Osmylation of chiral cis-cyclohexadienediols

New Journal of Chemistry

Volumn 23, Issue 5, 1999, Pages 549-556

  Brovetto, Margarita ^a   Schapiro, Valeria ^a   Cavalli, Gabriel ^a   Padilla, Paula ^a   Sierra, Ana ^a   Seoane, Gustavo ^a   Suescun, Leopoldo ^a   Mariezcurrena, Raul ^a  

^a UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE DERIVATIVE; OSMIUM;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHIRALITY; CIS ISOMER; CRYSTAL STRUCTURE; ELECTRON; HYDROXYLATION; PRIORITY JOURNAL; STOICHIOMETRY;

EID: 0032765533     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/a900732f     Document Type: Article

References (50)

1. (a) G. N. Sheldrake, in Chirality in Industry, ed. A. N. Collins, G. N. Sheldrake and J. Crosby, J. Wiley & Sons Ltd, Chichester, 1992, p. 127.
2. (b) H. A. J. Carless, Tetrahedron: Asymmetry, 1992, 3, 795.
3. (c) S. M. Brown and T. Hudlicky, in Organic Synthesis: Theory and Applications, ed. T. Hudlicky, JAI Press, Inc., Greenwich, CT, 1993, vol. 2, p. 113.
4. (d) J. W. Reed and T. Hudlicky, in Advances in Asymmetric Synthesis, ed. A. Hassner, JAI Press, Inc., Greenwich, CT, 1995, vol. 1, p. 271.
5. (e) T. Hudlicky, in Green Chemistry: Designing Chemistry for the Environment, ed. P. T. Anastas and T. Williamson, ACS Symposium Series No 626, American Chemical Society, Washington, DC, 1996, p. 180.
6. (f) T. Hudlicky and A. J. Thorpe, Chem. Commun., 1996, 1993.
7. See for example ref. 1f and: (a) L. A. Paquette and H.-C Tsui, Synlett, 1996, 129.
8. (b) D. González, V. Schapiro, G. Seoane, T. Hudlicky and K. Abboud, J. Org. Chem., 1997, 62, 1194.
9. (c) M. Desjardins, M. C. Lallemand, T. Hudlicky and K. Abboud, Synlett, 1997, 728.
10. (d) F. Yan, B. V. Nguyen, C. York and T. Hudlicky, Tetrahedron, 1997, 53, 11541.
11. For reviews: (a) M. Schröder, Chem Rev., 1980, 80, 187.
12. (b) H. C. Kolb, M. S. Van Nieuwenhze and K. B. Sharpless, Chem Rev., 1994, 94, 2483.
13. (a) C. Y. Park, B. M. Kim and K. B. Sharpless, Tetrahedron Lett., 1991, 32, 1003.
14. (b) see also K. Narkuhan and M. Nagarajan, J. Chem. Soc., Chem. Commun., 1994, 1705.
15. (c) D. Xu, G. A. Crispino and K. B. Sharpless, J. Am. Chem. Soc., 1992, 114, 7570.
16. (a) H. A. J. Carless, K. Busia, Y. Dove and S. S. Malik, J. Chem. Soc., Perkin Trans. 1, 1993, 2505.
17. (b) see also T. J. Donohoe, P. R. Moore and R. L. Beddoes, J. Chem. Soc., Perkin Trans. 1, 1997, 43.
18. It is accepted that for alkenes with a moderate steric hindrance, the steric factors prevail over the electronic ones, in the diastereo- selective control of the osmylation. See also R. L. Halterman and M. A. Mc Evoy, J. Am. Chem. Soc., 1992, 114, 980.
19. (a) J. K. Cha, W. J. Christ and Y. Kishi, Tetrahedron Lett., 1983, 24, 3943 and 3947.
20. (b) J. K. Cha, W. J. Christ and Y. Kishi, Tetrahedron, 1984, 40, 2247.
21. (c) K. N. Houk, S. R. Moses, Y.-D. Wu, N. G. Rondau, V. Jager, R. Schone and F. R. Fronczek, J. Am. Chem. Soc., 1984, 106, 3880.
22. (d) K. N. Houk, H.-Y Duh, S. R. Moses and Y.-D. Wu, J. Am. Chem. Soc., 1986, 108, 2754.
23. (e) E. Vedejs and C. K Mc Clure, J. Am. Chem. Soc., 1986, 108, 1094.
24. (f) C. R. Johnson, B. D. Tait and A. S. Cieplak, J. Am. Chem. Soc., 1987, 109, 5875.
25. (g) E. Vedejs, and W. H. Dent III, J. Am. Chem. Soc., 1989, 111, 6861.
26. (a) D. J. Berrisford, C. Bolm and K. B. Sharpless, Angew. Chem., Int. Ed. Engl., 1995, 34, 1059.
27. (b) J. S. M. Wai, Y. Marko, J. S. Svendsen, M. G. Finn, E. N. Jacobsen and K. B. Sharpless, J. Am. Chem. Soc., 1989, 111, 1123.
28. (c) D. W. Nelson, A. Gypser, P. T. Ho, H. C. Kolb, T. Kondo, H.-L. Kwong, D. V. McGrath, A. E. Rubin, P.-O. Norrby, K. P. Gable and K. B. Sharpless, J. Am. Chem. Soc., 1997, 119, 1840.
29. W. B. Motherwell and A. Williams, Angew. Chem., Int. Ed. Engl., 1995, 34, 2031.
30. (a) D. T. Gibson, M. Hensley, H. Yoshika and R. J. Mabry, Biochemistry, 1970, 9, 1626.
31. (b) D. T. Gibson, G. J. Zylstra and S. Chauhan, in Pseudomonas: Biotransformations, Pathogenesis, and Evolving Biochemistry, ed. S. Silver, A. Chakrabarty, B. Iglewski and S. Kaplan, American Society for Microbiology, Washington, DC, 1990, p. 121.
32. (a) T. Hudlicky, J. D. Price and H. F. Olivo, Synlett, 1991, 645.
33. (b) A. J. Blacker, R. J. Booth, G. M. Davies and J. K. Sutherland, J. Chem. Soc., Perkin Trans. 1, 1995, 2861.
34. (a) H. A. J. Carless and Y. Dove, Tetrahedron: Asymmetry, 1996, 7, 649.
35. (b) C. H. Tran, D. H. G. Crout, W. Errington and G. M. Whited, Tetrahedron: Asymmetry, 1996, 7, 691.
36. 11b states that for a protected carbomethoxy cyclohexadienediol the regioselectivity was low, and this was ascribed to a rotation of the carbomethoxy group out of conjugation with the double bond, thus changing the electronic distribution in the dienic system.
37. (a) M. Cortes and G. Vernal, presented at the "XXII Congreso Latinoamericano de Química", Concepción, Chile, January 1996
38. (b) see also ref. 5b.
39. The osmylations of protected cyclohexadienediols reported in the literature deal with bulky protecting groups, such as acetonide, that shield completely one face of the molecule: T. Hudlicky, F. Rulin, T. Tsunoda, H. Luna, C. Andersen and J. D. Price, Isr. J. Chem., 1991, 31, 229.
40. S. B. King and B. Ganem, J. Am. Chem. Soc., 1994, 116, 562.
41. S. Russi, L. Suescun, A. Mombru, H. Pardo, R. Mariezcurrena, M. Brovetto and G. Seoane, Acta Crystallogr., Sect. C, 1999, 55, in press.
42. V. Van Rheenen, R. C. Kelly and D. Y. Cha, Tetrahedron Lett., 1976, 28, 1973.
43. (a) M. Burdisso and R. Gandolfi, Tetrahedron Lett., 1991, 32, 2659.
44. (b) D. A. Evans and S. W. Kaldor, J. Org. Chem., 1990, 55, 1698.
45. (a) T. Hudlicky, H. Luna, G. Barbieri and L. D. Kwart, J. Am. Chem. Soc., 1988, 110, 4735.
46. (b) see ref. 1b.
47. For a reaction run in aprotic media, where the possibility of hydrogen bonding may improve the syn selectivity, see ref. 5b and T. J. Donohoe, P. R. Moore, M. J. Waring and N. J. Newcombe, Tetrahedron Lett., 1997, 38, 5027.
48. T. Hudlicky, C. H. Boros and E. E. Boros, Synthesis, 1992, 174.
49. T. Hudlicky, H. Luna, J. D. Price and F. Rulin, J. Org. Chem., 1990, 55, 4683.
50. B. P. McKibben, G. S. Barnosky and T. Hudlicky, Synlett, 1995, 806.