Improving catalyst activity in secondary amine catalysed transformations

John B. Brazier, Timothy J. K. Gibbs, Julian H. Rowley, Leopold Samulis, Sze Chak Yau, Alan R. Kennedy, James A. Platts, Nicholas C. O. Tomkinson

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)
54 Downloads (Pure)


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.
Original languageEnglish
Pages (from-to)133-141
Number of pages9
JournalOrganic and Biomolecular Chemistry
Issue number1
Early online date14 Oct 2014
Publication statusPublished - 7 Jan 2015


  • catalyst performance
  • catalyst activity
  • cycloaddition


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