Rapid access to piperidinones via allylic oxidation of enamides

ORGN 105

Darren Bykowski, dbykowsk@mail.umd.edu, Arthur J. Catino, acatino@umd.edu, Jason M. Nichols, jnicholz@umd.edu, Nischal Sidhu, Sidhartha Gottipamula, and Michael P. Doyle, mdoyle3@umd.edu. Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742
Substituted piperidines are ubiquitous structures found in natural products and biologically active compounds. The use of piperidinones as the corresponding synthetic precursors remains largely unexploited due to the lack of a convenient, general route to polyfunctionalized piperidinones. We have previously demonstrated that dirhodium caprolactamate [Rh2(cap)4] catalyzes the allylic oxidation of olefins. We now report an extension of this methodology to enamides, providing access to a variety of functionalized piperidinones. Elaboration of the piperidinones into pharmacologically active compounds will also be described.


New Reactions and Methodology, Materials, Total Synthesis, Process R&D
8:00 PM-10:00 PM, Sunday, 28 August 2005 Washington DC Convention Center -- Hall A, Poster

8:00 PM-10:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005