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


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.

SUBMITTER: Hicks EF 

PROVIDER: S-EPMC12333383 | biostudies-literature | 2025 Aug

REPOSITORIES: biostudies-literature

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

Hicks Elliot F EF   Fuentes Ruiz Leanne M LM   Gaskins Bryce E BE   Takase Michael K MK   Stoltz Brian M BM  

The Journal of organic chemistry 20250718 30


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 aziridi  ...[more]

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