ORGN 461 |
| Multi-component coupling reactions mediated by a palladium catalyst constitute important synthetic tools. Recently we have reported a new protocol, in which a single p-allylpalladium catalyst combines two building blocks to form an unsymmetrical bis-p-allylpalladium complex I. This complex subsequently mediates a regioselective allyl transfer to electrophiles providing either branched homoallylic alcohols or a,b-unsaturated-d-lactones. Herein, we wish to report an extension to our methodology for the incorporation of imino esters providing highly substituted homoallylic amino esters II. The scope of the methodology with respect to structures of boronic acids, allenes and the protecting group on the nitrogen will be presented. The possibility to replace the p-allylpalladium catalysts with commercially available palladium(II) sources accompanied by optimized monodentate phosphine ligands will be discussed. The progress towards the elaboration of the amino esters II to cyclic amino acids related to biologically active targets will be presented.
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Metal-Mediated Reactions and Syntheses
8:00 AM-12:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- C302, Oral
Division of Organic Chemistry |
