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Synfacts 2005(1): 0117-0117  
DOI: 10.1055/s-2005-872197
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

A Stereospecific Synthesis of Imidazolidin-2-ones from Aziridine-2-carboxylates and Isocyanates

Contributor(s): Victor Snieckus, Robert Engqvist
M. S. Kim, Y.-W. Kim, H. S. Hahm, J. W. Jang, W. K. Lee*, H.-J. Ha*
Sogang University, Seoul and Hankuk University of Foreign Studies, Yongin, Korea
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Publication History

Publication Date:
21 September 2005 (online)

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Significance

A mild, Lewis acid (MgBr2 or TMSCl)­ catalyzed regiospecific and stereospecific reaction of aziridine-2-carboxylates with isocyanates to afford imidazolidin-2-ones is reported. Although aziridine ring expansion reactions are common, stereospecific processes are relatively rare (J.-O. Baeg, C. Bensimon, H. Alper J. Am. Chem. Soc. 1995, 117, 4700-4701). The reaction proceeds with retention of configuration controlled by the α-benzylamine chiral auxiliary in good to excellent yields.