Ruthenium-Catalyzed Flash Oxidation of Allenes to α,α′-Dihydroxyketones

Article abstract of DOI:10.1055/s-1997-5759

The ruthenium-catalyzed flash oxidation of β-allenic esters 1 furnishes α,α′-dihydroxyketones 2 in 24-72% yield. In the case of the chiral allene 1e, the oxidation proceeds with good diastereoselectivity (88% de), i.e. with efficient axis to center chirality transfer. The flash oxidation can also be used for the synthesis of corticosteroids, as exemplified by the transformation of allenic steroid 4 into dihydroxyketone 5.