Allylic Oxidation of Steroidal Compounds Using Vanadyl Acetylacetonate and Tert-butyl Hydroperoxide

Abstract

Allylic oxidation is an important reaction in steroid chemistry. Previously reported methods have various limits which do not apply when using vanadyl acetylacetonate and tert-butyl hydroperoxide. These limits include costs, need for inert environments, short half-lives of catalysts, over-oxidation, need for protection groups, and low yields. Vanadyl acetylacetonate is inexpensive and shelf stable. Here, we describe the novel use of vanadyl acetylacetonate for oxidation of a variety of ∆5 steroidal olefins, without protection groups, in ambient atmosphere and at room temperature.