The effect on catalyst performance of altering substituents at the 2-position of the Macmillan imidazolidinone has been examined. Condensation of L-phenylalanine N-methyl amide with acetophenone derivatives results in a series of imidazolidinones whose salts can be used to accelerate the Diels-Alder cycloaddition. Electron withdrawing groups significantly increases the overall rate of cycloaddition without compromise in selectivity. The most effective catalyst was shown to be efficient for a variety of substrates and the applicability of this catalyst to alternative secondary amine catalysed transformations is also discussed.
- catalyst performance
- catalyst activity
Brazier, J. B., Gibbs, T. J. K., Rowley, J. H., Samulis, L., Yau, S. C., Kennedy, A. R., Platts, J. A., & Tomkinson, N. C. O. (2015). Improving catalyst activity in secondary amine catalysed transformations. Organic and Biomolecular Chemistry, 13(1), 133-141. https://doi.org/10.1039/C4OB01916D