ArticleAngewandte Chemie (International ed. in English)2017
A Stereoselective [3+1] Ring Expansion for the Synthesis of Highly Substituted Methylene Azetidines.
Article in Angewandte Chemie (International ed. in English), 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
20 citing papers in PubMed.
- Reactivity of Anomalous Aziridines for Versatile Access to High FspAccounts of chemical research · 2025Article
- Asymmetric one-carbon ring expansion of diverse N-heterocycles via copper-catalyzed diyne cyclization.Science advances · 2024Article
- Stereoselective polar radical crossover for the functionalization of strained-ring systems.Communications chemistry · 2024Article
- Tunable Divergent Reactivity of Aziridinium Ylides in the Synthesis of Complex Piperidines and Azetidines.ACS catalysis · 2024Article
- Article
- Azetidine synthesis enabled by photo-induced copper catalysis via [3+1] radical cascade cyclization.Innovation (Cambridge (Mass.)) · 2022Article
- 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
- Catalytic asymmetric cycloaddition reactions of enoldiazo compounds.Organic & biomolecular chemistry · 2019Review
- α-Tetrasubstituted Aldehydes through Electronic and Strain-Controlled Branch-Selective Stereoselective Hydroformylation.The Journal of organic chemistry · 2018Article
- Ring Expansion of Bicyclic Methyleneaziridines via Concerted, Near-Barrierless [2,3]-Stevens Rearrangements of Aziridinium Ylides.ACS catalysis · 2018Article
- Blue light-promoted photolysis of aryldiazoacetates.Chemical science · 2018Article
- A high-activity cobalt-based MOF catalyst for [2 + 2 + 2] cycloaddition of diynes and alkynes: insights into alkyne affinity and selectivity control.RSC advances · 2018Article
- Oxidative allene amination for the synthesis of nitrogen-containing heterocycles.ARKIVOC : free online journal of organic chemistryArticle
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
3 authors.
Funding
Abstract
The reaction of rhodium-bound carbenes with strained bicyclic methylene aziridines results in a formal [3+1] ring expansion to yield highly substituted methylene azetidines with excellent regio- and stereoselectivity. The reaction appears to proceed through an ylide-type mechanism, where the unique strain and structure of the methylene aziridine promotes a ring-opening/ring-closing cascade that efficiently transfers chirality from substrate to product. The resultant products can be elaborated into new azetidine scaffolds containing vicinal tertiary-quaternary and even quaternary-quaternary stereocenters.
Indexed as
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.