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Diastereoselective one-pot synthesis of tetrafunctionalized 2-imidazolines

, : Diastereoselective one-pot synthesis of tetrafunctionalized 2-imidazolines. Journal of Organic Chemistry 79(11): 5219-5226

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.


PMID: 24820129

DOI: 10.1021/jo500790n

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