Abstract
A series of sterol esters bearing varying patterns of unsaturation on the nucleus, side chain, and acyl substituent were epoxidized using trans-dioxoruthenium(VI) tetramesitylporphyrin as catalyst and air as source of oxygen. Attack at the steroid nucleus is generally favored, and a high degree of β-stereoselectivity is obtained except for conjugated 5,7 diene systems which yield a ca. 1∶1 mixture of 5,6α and 5,6β epoxides.
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Tavares, M., Ramasseul, R. & Marchon, JC. Regioselective epoxidation by air of sterol esters bearing several double bonds using a ruthenium porphyrin catalyst. Catal Lett 4, 163–167 (1990). https://doi.org/10.1007/BF00765699
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DOI: https://doi.org/10.1007/BF00765699