Diastereoselective one-pot synthesis of tetrafunctionalized 2-imidazolines

Guido V. Janssen, Paul Slobbe, Maurice Mooijman, Art Kruithof, Andreas W. Ehlers, Célia Fonseca Guerra, F. Matthias Bickelhaupt, J. Chris Slootweg, Eelco Ruijter, Koop Lammertsma, Romano V.A. Orru

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)


A convenient trans-selective one-pot synthesis of tetrafunctionalized 2-imidazolines is described. Our approach to these valuable heterocyclic scaffolds involves a formal 1,3-dipolar cycloaddition between nitrile ylides or nitrilium triflates and imines. A detailed experimental study in combination with a high-level computational exploration of reaction routes reveals a plausible reaction pathway that accounts for the observed diastereoselectivity.

Original languageEnglish
Pages (from-to)5219-5226
Number of pages8
JournalJournal of Organic Chemistry
Issue number11
Publication statusPublished - 6 Jun 2014
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry


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