Diastereoselective One-Pot Synthesis of Tetrafunctionalized 2-Imidazolines

作者:Janssen Guido V; Slobbe Paul; Mooijman Maurice; Kruithof Art; Ehlers Andreas W; Guerra Celia Fonseca; Bickelhaupt F Matthias; Slootweg J Chris; Ruijter Eelco; Lammertsma Koop*; Orru Romano V A
来源:Journal of Organic Chemistry, 2014, 79(11): 5219-5226.
DOI:10.1021/jo500790n

摘要

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.

  • 出版日期2014-6-6