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Communication | Special issue | Vol 90, No. 2, 2015, pp.874-882
Published online, 10th September, 2014
DOI: 10.3987/COM-14-S(K)96
■ Efficient Preparation of a Versatile Chiral Synthon for 1,2-Diamines via the Fe(III)-Catalyzed Diastereoselective Oxidation of 2-Imidazolone and Its Application

Hirofumi Matsunaga,* Iori Eshita, 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

Abstract

The efficient and predominant preparation of (4S,5S)-4,5-dimethoxy-2-imidazolidinone (DMIm) was established via the Fe(III)-catalyzed diastereoselective oxidation of 1-[(1S,2R)-2-exo-alkoxyapocamphanecarbonyl]-2-imidazolone with aqueous H2O2 up to 94% d.e., both of which were easily purified by column chromatography, followed by simple and convenient conversions. The obtained N-tosyl-(4S,5S)-DMIm proved to be a versatile chiral synthon for 1,2-diamines by the synthesis of (1S,2S)-1,2-diamino-1-(4-fluorophenyl)butane derivative, whose platinum complex showed potent antitumor activity.