Oxidative Mannich reaction catalyzed by dirhodium caprolactamate

ORGN 632

Arthur J. Catino, acatino@umd.edu, Jason M. Nichols, jnicholz@umd.edu, Brian J. Nettles, and Michael P. Doyle, mdoyle3@umd.edu. Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742
Dirhodium caprolactamate [Rh2(cap)4] is a highly effective catalyst for the oxidative Mannich reaction involving the catalytic C-H oxidation of a tertiary amine to an iminium ion followed by capture with a nucleophile (Nuc). Reactions are performed efficiently (0.1 – 1.0 mol% catalyst loading) in combination with inexpensive T-HYDRO (70% t-BuOOH in water). We have recently communicated the preparation of aminoalkyl butenolides from 2-siloxyfurans using this methodology, and further extensions in synthetic applicability will be reported.

 

New Reactions and Methodology
8:00 AM-12:00 PM, Wednesday, 13 September 2006 Moscone Center -- Room 133, Oral

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006