Epoxidation of cholesteryl acetate (3) with pyridine–trifluoroacetic anhydride–molecular oxygen afforded bis(trifluoroacetate)(4), β-epoxide (5], α-epoxide (6), hydroxy trifluoroacetates A (7) and B (9), and enone (8). An oxidation mechanism proceeding via the hydroperoxide intermediate (A) is presented.
T. Harayama, O. Sakurai, H. Fukushi, Y. Tezuka and F. Yoneda, J. Chem. Soc., Perkin Trans. 1, 1988, 2335 DOI: 10.1039/P19880002335
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