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

Full text not available in this repository.Request a copy from the Strathclyde author

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).