Development of the highly efficient iron-catalyzed asymmetric reaction system aimed for the versatile synthesis of chiral compounds of biological interest

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A new method was established for the preparation of trans-4,5-dimethoxy-2-imidazolidinone (DMIm), versatile chiral synthon for the preparation of various optically active 1,2-diamines which were very useful in the field of pharmaceutical and/or agrochemical science, via the Fe(III)-catalyzed oxidation of 2-imidazolone by H2O2-urea followed by the subsequent optical resolution via the introduction of a MAC moiety. Chiral DMIm was also available from highly diastereoselective Fe-catalyzed oxidation of chiral 2-imidazolone. Enantioselective oxidation of trans-stilbene catalyzed by chiral "roofed" cis-1,2-diamine-iron complex was tried and moderate enantioselectivity was achieved.