ArticleNature communications2024
Enantioselective formal (3 + 3) cycloaddition of bicyclobutanes with nitrones enabled by asymmetric Lewis acid catalysis.
Article in Nature communications, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
What it found
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The trial behind it
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Who cites it
8 citing papers in PubMed.
- Pd-Catalyzed De Novo Skeletal Editing of Bicyclic Carbamates Delivers 2-Pyrimidinones.Organic letters · 2026Article
- Beyond para- and meta-Substitution: Synthesis and Biological Validation of Chalcogen-Rich Thiabicyclo[3.1.1]heptanes as Bioisosteres of Aryl Thioether Derivatives.Angewandte Chemie (International ed. in English) · 2026Article
- Switchable annulation paths to diverse N-bridged bicyclic scaffolds via ligand-directed dicarbonylation.Nature communications · 2026Article
- Collective synthesis of 1,2,4-trisubstituted, meta- and ortho-substituted arene bioisosteres from bicyclobutanes.Nature chemistry · 2026Article
- Hetero[3.1.1]propellanes.Nature chemistry · 2026Article
- Lewis Acid-Catalyzed Divergent (4+3)/(4+2) Annulations ofOrganic letters · 2026Article
- Regiodivergent hydrophosphination of Bicyclo[1.1.0]-Butanes under catalyst control.Nature communications · 2025Article
- Article
Corrections and comments
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Authors and funding
7 authors.
Funding
Abstract
The absence of catalytic asymmetric methods for synthesizing chiral (hetero)bicyclo[n.1.1]alkanes has hindered their application in new drug discovery. Here we demonstrate the achievability of an asymmetric polar cycloaddition of bicyclo[1.1.0]butane using a chiral Lewis acid catalyst and a bidentate chelating bicyclo[1.1.0]butane substrate, as exemplified by the current enantioselective formal (3 + 3) cycloaddition of bicyclo[1.1.0]butanes with nitrones. In addition to the diverse bicyclo[1.1.0]butanes incorporating an acyl imidazole group or an acyl pyrazole moiety, a wide array of nitrones are compatible with this Lewis acid catalysis, successfully assembling two congested quaternary carbon centers and a chiral aza-trisubstituted carbon center in the pharmaceutically important hetero-bicyclo[3.1.1]heptane product with up to 99% yield and >99% ee.
Identifiers
What Socratic 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 Socratic graph.