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

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

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

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

DOI: 10.1021/ja045330o (free Supporting Information)


Abstract

Dirhodium(II) caprolactamate effectively catalyzes the allylic oxidation of a variety of olefins and enones with tert-butyl hydroperoxide as terminal oxidant. The reaction is completely selective, tolerant of air and moisture, and can be performed with as little as 0.1 mol % catalyst in minutes.

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

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


Key Words

Enones, tert-butyl hydroperoxide


ID: J48-Y2004-1790