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 (https://doi.org/10.1002/anie.201005892)

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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;
  • Item type:Article
    ID code:33042
    Dates:
    Date
    Event
    11 February 2011
    Published
    Notes:M1 - Copyright (C) 2011 U.S. National Library of Medicine. MEDLINE AN 2011182003(Journal; Article; (JOURNAL ARTICLE))
    Keywords:Diels–Alder reaction , imidazolidinone , iminium ion catalysis, organocatalysis, Chemistry, Medicine(all)
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:30 Aug 2011 09:03
    Last modified:12 May 2022 00:25
    URI:https://strathprints.strath.ac.uk/id/eprint/33042
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