Palladium-Catalyzed Stereoselective Allylic Alkylation of Carboxylic Acids, Esters, and Nitriles

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The chemistry of 'hard', nonstabilized enolates and that of allylpalladium complexes was developed about the same time. Nevertheless, anionic enolates and cationic allyl complexes were not considered suitable, compatible reactants. Only during the last decade - also by contributions of our research group - the stereoselective allylic alkylation was extended to nonstabilized enolates of ketones, amides, lactams, and lactones as well as dianions of carboxylic acids, classified as particularly 'hard' nucleophiles (the latter two classes of compounds in the preceding project).Among the classic derivatives of carboxylic acids, there remain two that have - at least not in a general way - been employed in the palladium-catalyzed allylic alkylation: esters and nitriles. Filling this gap is the principle aim of the project on hand. If this goal will be reached, as indicated by our spadework, the scope and versatility of the allylic alkylation would be enhanced considerably, thus permitting to perform novel useful diastereoselective and enantioselective carbon-carbon bond formation reactions.