Abstract
The electrostatic effect of the solvent on the reaction of cyclopentadiene with methyl acrylate has been studied with the help of a Self-Consistent Reaction Field model by means of ab initio computations. The effect on the reaction mechanism, endo/exo selectivity, and activation energy has been analyzed. Moreover, the computations allow a discussion of the solvent effect on the diastereofacial selectivity when chiral acrylates are used and a omparison with experimental data for the reaction of cyclopentadiene with (-)-menthyl acrylate. The results are in agreement with the experimentally observed increase of the endo/exo and diastereofacial selectivities as a function of solvent polarity, but hydrophobic effects and hydrogen-bond formation are necessary to account for changes in reaction rates
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