On the roles of protic solvents in imidazolidinone-catalyzed transformations

Brazier, John B. and Jones, Kevin M. and Platts, James A. and Tomkinson, Nicholas C.O. (2011) On the roles of protic solvents in imidazolidinone-catalyzed transformations. Angewandte Chemie, 50 (7). pp. 1613-1616. ISSN 0044-8249

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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).

ORCID iDs

Brazier, John B., Jones, Kevin M., Platts, James A. and Tomkinson, Nicholas C.O. ORCID logoORCID: https://orcid.org/0000-0002-5509-0133;