Palladium and Nickel-Catalyzed Transformations Accessing Electron-Rich Allylmetal Intermediates

The investigation of pre-formed NHC-ligated allylpalladium complexes and their use as efficient catalysts in the context of a conjugate allylation of &agr;,beta-unsaturated N-acylprroles will be discussed. A second project, utilizing in situ generated nickel and palladium catalysts, will demonstrate that both metals are competent in a formal [3+2] cycloaddition, forming 1,3-oxazolidines in a stereoselective process. A common theme intertwining these projects is differential catalytic access, depending upon the ligand and metal utilized, to both nucleophilic and electrophilic reactivity. The ability to comprehend and harness this reactivity is the basis for this dissertation.