The First Catalytic Enantioselective Synthesis of cis-Epoxyketones from cis-Enones.-Epoxidation of cis-enones (II) and (V) with tert-butyl hydroperoxide catalyzed by ytterbium-3-hydroxymethyl-BINOL complex (Ib) proceeds with excellent diastereo-and enantioselectivity to afford the cis-(S,S)-epoxyketones (III) and (VI). Interestingly, the corresponding cis-(R,R)-enantiomers are obtained in the presence of an ytterbium-BINOL complex (Ia).
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