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Updated: Sep 28, 2025

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Copper Catalyzed Regioselective and Stereospecific Aziridine Opening with Pyridyl Grignard Nucleophiles
Jaehee Lee1, Xuan Ju1, Miseon Lee1
1Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States.
Abstract:
Copper catalyzed regioselective and stereospecific coupling between aziridines and in situ generated pyridine Grignard reagents is reported. This method provides β-pyridylethylamines with diverse structures and functionalities from aziridines and iodopyridines. β-Pyridylethylamines are potential scaffolds for the synthesis of biologically active compounds often found in pharmaceuticals. The synthesis of challenging chiral dihydroazaindoles was also achieved through mild one-pot reaction conditions via aziridine opening followed by nucleophilic cyclization.
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