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 journalArticle

21 Citations (Scopus)
7 Downloads (Pure)

Abstract

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
Volume50
Issue number7
DOIs
Publication statusPublished - 11 Feb 2011

Keywords

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

Fingerprint Dive into the research topics of 'On the roles of protic solvents in imidazolidinone-catalyzed transformations'. Together they form a unique fingerprint.

Cite this