On the roles of protic solvents in imidazolidinone-catalyzed transformations

John B. Brazier, Kevin M. Jones, James A. Platts, Nicholas C.O. Tomkinson

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)
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The effect of protic solvents on the rate and stereochemical outcome of the imidazolidinone-catalyzed Diels–Alder cycloaddition was rationalized. The following picture emerges: the solvent accelerates iminium ion formation (step 1), the Diels–Alder cycloaddition is reversible (step 2), and the solvent intercepts the iminium ion adduct (step 3).
Original languageEnglish
Pages (from-to)1613-1616
Number of pages4
JournalAngewandte Chemie
Issue number7
Publication statusPublished - 11 Feb 2011


  • Diels–Alder reaction
  • imidazolidinone
  • iminium ion catalysis
  • organocatalysis


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