ArticleACS catalysis2018
Ring Expansion of Bicyclic Methyleneaziridines via Concerted, Near-Barrierless [2,3]-Stevens Rearrangements of Aziridinium Ylides.
Article in ACS catalysis, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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13 citing papers in PubMed, 56 citations in OpenAlex.
- E/Z Isomerization-Enabled Conversion from Dual-Carbon to Single-Carbon Insertion into an Aromatic System.JACS Au · 2026Article
- Difluorocarbene-induced [1,2]- and [2,3]-Stevens rearrangement of tertiary amines.Nature communications · 2024Article
- Tunable Divergent Reactivity of Aziridinium Ylides in the Synthesis of Complex Piperidines and Azetidines.ACS catalysis · 2024Article
- Article
- Biocatalytic One-Carbon Ring Expansion of Aziridines to Azetidines via a Highly Enantioselective [1,2]-Stevens Rearrangement.Journal of the American Chemical Society · 2022Article
- Tunable Aziridinium Ylide Reactivity: Non-covalent Interactions Enable Divergent Product Outcomes.ACS catalysis · 2022Article
- Copper-catalyzed [3 + 1] cyclization of cyclopropenes/diazo compounds and bromodifluoroacetamides: facile synthesis of α,α-difluoro-β-lactam derivatives.Chemical science · 2021Article
- Synthetic Applications of Aziridinium Ions.Molecules (Basel, Switzerland) · 2021Review
- Synthesis and applications of methyleneaziridines.RSC advances · 2020Review
- Aziridinium Ylides: Underutilized Intermediates for Complex Amine Synthesis.Trends in chemistry · 2020Article
- Rh-Catalyzed Aziridine Ring Expansions to Dehydropiperazines.Organic letters · 2020Article
- Intermolecular [3+3] ring expansion of aziridines to dehydropiperi-dines through the intermediacy of aziridinium ylides.Nature communications · 2020Article
- Oxidative allene amination for the synthesis of nitrogen-containing heterocycles.ARKIVOC : free online journal of organic chemistryArticle
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4 authors at 2 institutions in 2 countries.
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Abstract
The synthesis of densely functionalized azetidinesin a highly stereocontrolled manner is challenging, but interest in the bioactivities of these small heterocycles has stimulated methods for their preparation. We recently reported a one-carbon ring expansion of bicyclic methylene aziridines under dirhodium catalysis capable of delivering enantioenriched azetidines. This work explores this ring expansion using computational and experimental studies. DFT computations indicate that the reaction proceeds through formation of an aziridinium ylide, which is precisely poised for concerted, asynchronous ring-opening/closing to deliver the azetidines in a [2,3]-Stevens-type rearrangement. The concerted nature of this rearrangement is responsible for the stereospecificity of the reaction, where axial chirality from the initial allene substrate is transferred to the azetidine product with complete fidelity. The computed mechanistic pathway highlights the key roles of the olefin and the rigid structure of the methylene aziridine in differentiating our observed ring expansion from competing cheletropic elimination pathways noted with ylides derived from typical aziridines.
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