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The synthesis of chiral compounds with the aid of benign organic catalysts is an important scientific goal. One important asymmetric carbon-carbon bond forming reaction which uses organocatalysts is the Stetter reaction. It has been shown that nucleophilic carbenes are very good organocatalysts for this reaction and we have carried out computational studies in order to understand better the mechanism of this process. In particular we have investigated electronic and steric effects which might be able to enhance and control the enantioselectivity of the reaction. This presentation will include an evaluation of the free energies of activation of the asymmetric step of a series of small model Stetter reactions and a discussion of the factors affecting enantioselectivity.
