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Improved chromium-catalyzed allylic oxidation of Δ-steroids with t-butyl hydroperoxide |
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| Authors: | Manolis A. Fousteris Anna I. Koutsourea Sotiris S. Nikolaropoulos Abdelkhalek Riahi Jacques Muzart |
| Affiliation: | aLaboratory of Medicinal Chemistry, School of Health Sciences, Department of Pharmacy, University of Patras, 26500 Patras, Greece bUnité Mixte de Recherche “Réactions Sélectives et Applications”, Boîte no. 44, CNRS-Université de Reims Champagne-Ardenne, B.P. 1039, 51687 Reims Cedex 2, France |
| Abstract: | Various chromiumVI-catalyzed conditions have been tested to improve the oxidation of Δ5-steroids with t-BuOOH to their corresponding 5-en-7-ones. The use of PDC or the association of CrO3 with an amine as the catalyst and CH2Cl2 or PhCF3 as the solvent led usually to the best yields. A minor reaction pathway was the epoxidation of the double bond. |
| Keywords: | Δ5-Steroids Allylic oxidation Catalysis Chromium oxides Tert-butyl hydroperoxide |
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