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Efficient Aziridination of Olefins Catalyzed by Mixed-Valent Dirhodium(II,III) Caprolactamate

Arthur J. Catino, Jason M. Nichols, Raymond E. Forslund and Michael P. Doyle*

*Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, Email: mdoyle3umd.edu

A. J. Catino, J. M. Nichols, R. E. Forslund, M. P. Doyle, Org. Lett., 2005, 7, 2787-2790.

DOI: 10.1021/ol0510973 (free Supporting Information)


Abstract

A mild, efficient, and selective aziridination of olefins with p-toluenesulfonamide catalyzed by dirhodium(II) caprolactamate is described. Aziridine formation occurs through aminobromination and subsequent base-induced ring closure.

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Dirhodium(II) Caprolactamate: An Exceptional Catalyst for Allylic Oxidation

A. E. Lurain, A. Maestri, A. R. Kelli, P. J. Carroll, P. J. Walsh, J. Am. Chem. Soc., 2004, 126, 13622-13623.


Key Words

Aziridinations


ID: J54-Y2005-750