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Synlett 1997; 1997(7): 765-766
DOI: 10.1055/s-1997-5759
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Ruthenium-Catalyzed Flash Oxidation of Allenes to α,α'-Dihydroxyketones

Michael Laux, Norbert Krause*
  • *Kekulé-Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Strasse 1, D-53121 Bonn, Germanx, FAX: 49-228-735683; E-Mail: krause@uni-bonn.de
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Publication Date:
31 December 2000 (online)

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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.

allenes - oxidation - ruthenium catalysis - chirality transfer - corticosteroids

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