Abstract
Cholest-5-ene-3-one1 is oxidized by air at room temperature in the presence of trans-di-oxoruthenium(VI)tetramesitylporphyrin Ru(O)2 (tmp) to a mixture of the 6β- and 6α-alcohols3 and4, and of the enedione5. Similar results are obtained in the presence of carbonylruthenium(II)tetramesitylporphyrin Ru(CO) (tmp) as catalyst. Iron(III) and manganese(III) tetramesitylporphyrins are weakly active or inactive as catalysts for the aerobic oxidation of1. Similarly, 17β-acetoxy-estr-5(10)-ene-3-one2 is oxidized to 17β-acetoxy-10β-hydroxyestr-4-ene-3-one7 in 42% yield in a highlyβ-stereoselective manner in the presence of Ru(O)2 (tmp).
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Tavares, M., Ramasseul, R., Marchon, JC. et al. Catalytic oxygenation ofβ,γ-unsaturated 3-ketosteroids in the presence of ruthenium tetramesitylporphyrin complexes. Catal Lett 8, 245–251 (1991). https://doi.org/10.1007/BF00764123
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DOI: https://doi.org/10.1007/BF00764123