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Updated: Sep 18, 2025

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Catalytic, Enantioselective Aziridine Desymmetrization with Pyrroles
Dustin Mauldin1, Ha Nguyen1, Ernest Brubaker1
1Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Dobo Hall, Wilmington, North Carolina 28403, United States.
Abstract:
Ring-opening reactions of meso-aziridines with carbon nucleophiles lead to complex, enantioenriched chiral amine derivatives through enantioselective catalysis. We report that a diphosphine-palladium(II) catalyst enables the highly enantioselective desymmetrization of N-acylaziridines with pyrroles. The β-pyrrole amine products are isolated with excellent enantioselectivity and varying yields across a range of pyrrole and aziridine substitution patterns. The synthetic utility of the pyrrole products is demonstrated by conversion to a novel saturated pyrrolopyridine core.
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