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    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.


    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. Diastereoselective one-pot synthesis of tetrafunctionalized 2-imidazolines. The Journal of organic chemistry. 2014 Jun 6;79(11):5219-26

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    PMID: 24820129

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