DOI: 10.1039/A902935D
(Paper)
Reference Section for: J. Chem. Res. (S), 1999, 538-539
The Transannular Effect of One Androstane Epoxide on the Stereochemistry of a Second Epoxidation
(Note: The full text of this document is currently only available in the PDF Version )
James R. Hanson, Peter B. Hitchcock and Ismail Kiran
Abstract
The transannular directing effect of a 2α,3α-, 2β,3β- and 5α,6α-epoxide on the epoxidation of a 5-ene and a 2-ene, respectively, is shown to increase the proportion of epoxidation of the anti face of the alkene when compared to the unsubstituted 2- and 5-androstenes.
References
- K. W. Woods and P. Beak, J. Am. Chem. Soc., 1991, 113, 6281 CrossRef CAS.
- D. N. Kirk and M. P. Hartshorn, Steroid Reaction Mechanisms, Elsevier, Amsterdam, 1968, p. 71 Search PubMed.
- H. B. Henbest and R. A. L. Wilson, J. Chem. Soc., 1957, 1958 RSC.
- M. Mousseron-Canet and J. C. Guilleux, Bull. Soc. Chim. Fr., 1966, 3853 CAS.
- J. R. Hanson, P. B. Hitchcock and I. Kiran, J. Chem. Res., 1999, (S) 198; (M) 1082 Search PubMed.
- T. D. Organ and J. R. Hanson, J. Chem. Soc. C, 1970, 2473 RSC.
- M. M. Campbell, R. C. Craig, A. C. Boyd, I. M. Gilbert, D. S. Savage and T. Sleigh, J. Chem. Soc., Perkin Trans. 1, 1979, 3042 RSC.
- M. M. Cambell, R. C. Craig, A. C. Hoyd, I. M. Gilbert, R. T. Logan, J. Redpath, R. G. Roy, D. S. Savage and T. Sleigh, J. Chem. Soc., Perkin Trans. 1, 1979, 2235 RSC.
- K. D. Bingham, T. M. Blaiklock, R. C. B. Coleman and G. D. Meakins, J. Chem. Soc. C, 1970, 2330 RSC.
- A. D. Cross, J. Am. Chem. Soc., 1962, 84, 3206 CrossRef CAS.
- K. Tori, T. Komeno and T. Nakagawa, J. Org. Chem., 1964, 29, 1136 CAS.
- W. L. Daux, M. G. Erman, J. F. Griffin and M. E. Wolff, Cryst. Struct. Commun., 1976, 5, 775 Search PubMed.
- G. M. Sheldrick, SHELXS-97 Program for Crystal Structure Solution, University of Gottingen, Germany, 1997.
- G. M. Sheldrick, SHELXL-97 Program for Crystal Structure Refinement, University of Gottingen, Germany, 1997.