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
1.
WoodsK. W. and BeakP., J. Am. Chem. Soc., 1991. 113, 6281.
2.
KirkD. N. and HartshornM. P., Steroid Reaction Mechanisms, Elsevier, Amsterdam, 1968, p. 71.
3.
HenbestH. B. and WilsonR. A. L., J. Chem. Soc., 1957, 1958.
4.
Mousseron-CanetM. and GuilleuxJ. C., Bull. Soc. Chim. Fr., 1966, 3853.
5.
HansonJ. R., HitchcockP. B. and KiranI., J. Chem. Res., 1999, (S) 198; (M) 1082.
6.
OrganT. D. and HansonJ. R., J. Chem. Soc. C, 1970, 2473.
7.
CampbellM. M., CraigR. C., BoydA. C., GilbertI. M., SavageD. S. and SleighT., J. Chem. Soc. Perkin Trans. 1, 1979, 3042.
8.
CambellM. M., CraigR. C., HoydA. C., GilbertI. M., LoganR. T., RedpathJ., RoyR. G., SavageD. S. and SleighT., J. Chem. Soc., Perkin Trans. 1, 1979, 2235.
9.
BinghamK. D., BlaiklockT. M., ColemanR. C. B. and MeakinsG. D., J. Chem. Soc. C, 1970, 2330.
10.
CrossA. D., J. Am. Chem. Soc., 1962, 84, 3206.
11.
ToriK., KomenoT. and NakagawaT., J. Org. Chem., 1964, 29, 1136.
12.
DauxW. L., ErmanM. G., GriffinJ. F. and WolffM. E., Cryst. Struct. Commun., 1976, 5, 775.
13.
SheldrickG. M., SHELXS-97 Program for Crystal Structure Solution, University of Gottingen, Germany, 1997.
14.
SheldrickG. M., SHELXL-97 Program for Crystal Structure Refinement, University of Gottingen, Germany, 1997.
