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

Elliot F Hicks, Leanne M Fuentes Ruiz, Bryce E Gaskins, Michael K Takase, Brian M Stoltz

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Article in The Journal of organic chemistry, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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1 · What the graph read from it

What it found

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2 · The registry

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4 · The record

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5 · Who and what money

Authors and funding

5 authors.

Elliot F HicksDivision of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.

Leanne M Fuentes RuizDivision of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.

Bryce E GaskinsDivision of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.

Michael K TakaseDivision of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.

Brian M StoltzDivision of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.ORCID 0000-0001-9837-1528

Funding

The Synthesis of Bioactive Natural Products as a Driving Force for Discovery in Organic ChemistryR35GM145239 · NIGMS · CALIFORNIA INSTITUTE OF TECHNOLOGY · PI BRIAN M STOLTZ · 2022 to 2026

$3.1M

NIGMS NIH HHS R35 GM145239

6 · The paper itself

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.

Identifiers

PMID40679266

DOI10.1021/acs.joc.5c01051

PMCPMC12333383

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