Diastereoselective One-pot Synthesis of Tetra-Functionalized 2-Imidazolines

G.V. Janssen, P. Slobbe, M. Mooijman, A. Kruithof, A.W. Ehlers, C. Fonseca Guerra, F.M. Bickelhaupt, J.C. Slootweg, E. Ruijter, K. Lammertsma, R.V.A. Orru

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

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. © 2014 American Chemical Society.
Original languageEnglish
Pages (from-to)5219-5226
JournalJournal of Organic Chemistry
Volume79
Issue number11
DOIs
Publication statusPublished - 2014

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