Rhodium(I)-catalyzed Alder-ene reactions of allenic ynones

ORGN 401

Thomas O. Painter Jr., topst3@pitt.edu and Kay M. Brummond, kbrummon@pitt.edu. Department of Chemistry, University of Pittsburgh, 806 Chevron Science Center, 219 Parkman Ave., Pittsburgh, PA 15260
As part of our interest in transition metal-mediated cycloisomerization reactions we wish to further develop the rhodium catalyzed allenic Alder-ene reaction. We have recently expanded the scope of this reaction to include electron-deficient alkynes. Allenic ynones react under rhodium(I) conditions to afford cross-conjugated trienones in high yield and the reaction is generally tolerant of many types of substitution. Results of these studies will be presented and application of this methodology to the total synthesis of cassiol will also be discussed.


Bioorganic, Metal-Mediated Reactions, and Molecular Recognition
8:00 PM-10:00 PM, Tuesday, 30 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