[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, and Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, Kagawa, Japan 769-2193
Org. Lett., 2006, 8 (3), pp 379–382
DOI: 10.1021/ol052417l
Publication Date (Web): January 17, 2006
Copyright © 2006 American Chemical Society

 Tokyo University of Science.

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 Tokushima Bunri University.

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*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, ssaito@rs.kagu.tus.ac.jp

Abstract

Abstract Image

Cycloaddition of aziridines with isocyanates proceeded smoothly in the presence of a nickel catalyst, and five iminooxazolidine derivatives were isolated in good yields. The best result was obtained when the reaction was carried out in the presence of NiI2, and a longer reaction time allowed the isomerization of the iminooxazolidine to the corresponding imidazolidinone derivatives.

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History

  • Published In Issue February 02, 2006
  • Received October 6, 2005

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