title: Improving catalyst activity in secondary amine catalysed transformations.
abstract: 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 increase 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.
authors.affiliation: School of Chemistry, Main Building, Cardiff University, Park Place, Cardiff, CF10 3AT, UK.
authors.forename: John B
authors.initials: JB
authors.lastname: Brazier
authors.forename: Timothy J K
authors.initials: TJ
authors.lastname: Gibbs
authors.forename: Julian H
authors.initials: JH
authors.lastname: Rowley
authors.forename: Leopold
authors.initials: L
authors.lastname: Samulis
authors.forename: Sze Chak
authors.initials: SC
authors.lastname: Yau
authors.forename: Alan R
authors.initials: AR
authors.lastname: Kennedy
authors.forename: James A
authors.initials: JA
authors.lastname: Platts
authors.forename: Nicholas C O
authors.initials: NC
authors.lastname: Tomkinson