Epoxidation of 2-cyclohexen-l-one

Successful asymmetric epoxidation of 2-cyclohexen-l-one was achieved using /-butyl hydroperoxide, toluene, solid sodium hydroxide, and benzylquininium chloride. Cyclohexenone epoxide obtained in this manner has an e.e. of 20% ([ ] = -39°). 

Peroxo Fe(ni), Mn(III) and Ti(IV) porphyrins were reacted with a variety of electron-poor organic substrates in order to compare their activity with that of different metalloper-oxide complexes. Epoxidation of 2-cyclohexen-l-one and 2-methyl-1,4-naphthoquinone was observed, in 25 and 75% yield respectively, with the extremely nucleophilic Fe(III) complex . These results opened new perspectives in the oxidation mechanisms of some enzymatic reactions. 

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