Intermolecular Hydroacylation: A New Reaction for Organic Synthesis

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The hydroacylation of alkenes is an example of a growing number of transformations based on C-H bond activation. The transformation has the potential to be a powerful synthetic tool; it is promoted by a number of transition metal catalysts and is inherently atom-economic. The utility of the reaction is limited by the propensity of the key acyl-metal intermediates to undergo decarbonylation, producing reduced substrates and inactive catalysts.In this proposal we detail a new approach to intermolecular hydroacylation utilizing the stabilizing ability of a pendent heteroatom to allow the direct addition of alkyl aldehydes to a range of functionalised alkenes under mild conditions using low catalyst loadings. The key to developing a successful system is the formation of chelation stabilised acyl-metal intermediates. The basic reactivity will initially be studied, before investigations into diastereoselective and enantioselective processes are undertaken. A method of employing alcohol substrates directly in the process will also be investigated.