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[3+2] Cross-Coupling Reactions of Aziridines with Isocyanates Catalyzed by Nickel(II) Iodide

Takeshi Munegumi, Isao Azumaya, Takako Kato, Hyuma Masu and Shinichi Saito*

*Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo, Japan 162-8601, Email: ssaitors.kagu.tus.ac.jp

T. Munegumi, I. Azumaya, T. Kato, H. Masu, S. Saito, Org. Lett., 2006, 8, 379-382.

DOI: 10.1021/ol052417l (free Supporting Information)


Abstract

A nickel-catalyzed cycloaddition of aziridines with isocyanates proceeded smoothly to give iminooxazolidine derivatives in good yields. A longer reaction time allowed the isomerization of the iminooxazolidine to the corresponding imidazolidinone derivatives.

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Key Words

Aziridines, Isocyanates, N-Heterocycles, O-Heterocycles, Oxazolidinones, Imidazolidinones


ID: J54-Y2006-350