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Paper | Special issue | Vol 88, No. 2, 2014, pp.1337-1353
Published online, 27th September, 2013
DOI: 10.3987/COM-13-S(S)104
Highly Efficient Preparation of Both Enantiomers of Versatile Chiral Synthon for 1,2-Diamines via the Fe(III)-Catalyzed Oxidation of 2-Imidazolone

Hirofumi Matsunaga,* Iori Eshita, Shoichi Tsunoda, Naoko Ishimoto, Shin Ando, and Tadao Ishizuka*

*Department of Pharmaceutical Sciences, Graduate School of Life Sciences, Kumamoto University, 5-1 Oe-hon-machi, Kumamoto 862-0973, Japan


A new method was established for the preparation of both of the enantiomers of trans-4,5-dimethoxy-2-imidazolidinone (DMIm) via the Fe(III)-catalyzed oxidation of 2-imidazolone by H2O2-urea, which allowed the subsequent achievement of optical resolution via the introduction of a MAC moiety and a 2-mesitylenesulfonyl group at the two nitrogen positions of DMIm, which then were easily removed. The two enantiomers are useful as versatile chiral synthons for 1,2-diamines.