Rare earth metal complex catalyst asymmetric

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PROBLEM TO BE SOLVED : To asymmetrically epoxidize a hydroperoxide compound in a good yield by using a complex catalyst prepared from a rare earth metal alkoxide, etc. SOLUTION : (A) A compound having a carbon-carbon double bond adjacent to a carbonyl group and represented by the formula [R -R are each H, a (substituted) alkyl, a (substituted) cycloalkyl, a (substituted) alkenyl, etc.] is asymmetrically epoxidize with (C) a hydroperoxide compound in the presence of (B) a complex catalyst prepared from (i) an organic active dihydroxy compound or (ii) an organic active 1, 3-diketo compound and (iii) a rare earth metal alkoxide. Therein, the components (i) is preferably an optically active biaryl type bihydroxy compound of formula II [R R are each H, a (substituted) 1-6C alkyl, a (substituted) alkenyl, etc.], especially a (substituted) optically active binaphthol. The component (iii) is preferably triisopropoxide. The component C is preferably t-butylhydroxide, etc.