Catalytic Epoxidation of Enones Mediated by Zinc Alkylperoxide/tert-BuOOH Systems

The epoxidation of enones by zinc alkylperoxides is a challenging task receiving considerable attention in contemporary research; however, until now no well-defined zinc alkylperoxide based systems have been described. Here, a new catalytic method of epoxidation of enones in the presence of zinc alkylperoxides supported by N,N-bidentate ligands and tert-butyl hydroperoxide is reported. A new dimeric zinc alkylperoxide complex supported by an aminotroponiminate ligand is also presented. The studied catalytic systems show high activity in the epoxidation of trans-chalcone, and in the case of a chiral catalyst with the (S,S)-N,N′-bis­(1-phenylethyl)­aminotroponiminate ligand a moderate enantioselectivity was achieved.