Preparation and Regioselective Ring Opening Reactions of Fused Bicyclic N-Aryl Aziridines

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.