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Updated: Sep 15, 2025

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Preparation and Regioselective Ring Opening Reactions of Fused Bicyclic N-Aryl Aziridines
Elliot F Hicks1, Leanne M Fuentes Ruiz1, Bryce E Gaskins1
1Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
Abstract:
Presented herein is a systematic evaluation of ring opening reactions of bicyclic N-aryl aziridines. This class of compounds has not seen extensive study in the context of ring opening reactions making the site of reaction difficult to predict, potentially limiting their use as intermediates in the synthesis of nitrogen-containing molecules. Our recent successful ring opening strategy in the synthesis of hunterine A prompted us to systematically evaluate this transformation using related aziridines. Our findings show that ring opening reactions of bicyclic N-aryl aziridines occur with exquisite regioselectivity under a variety of conditions.
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