ArticleJournal of the American Chemical Society2023
Silver(I)-Catalyzed Synthesis of Cuneanes from Cubanes and their Investigation as Isosteres.
Article in Journal of the American Chemical Society, 2023. 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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Who cites it
13 citing papers in PubMed.
- Complete Computational Exploration of Eight-Carbon Hydrocarbon Chemical Space.The Journal of organic chemistry · 2026Article
- Collective synthesis of 1,2,4-trisubstituted, meta- and ortho-substituted arene bioisosteres from bicyclobutanes.Nature chemistry · 2026Article
- Polycyclic Scaffolds through the Intermediacy of Boron-Stabilized Nonclassical Carbocations.Journal of the American Chemical Society · 2025Article
- A Data-Driven Perspective on Bioisostere Evaluation: Mapping the Benzene Bioisostere Landscape with BioSTAR.Journal of medicinal chemistry · 2025Review
- On the Unexpected Formation of [2.2.1]- and [2.1.1]Homotriblattanes.Tetrahedron letters · 2025Article
- 3-Oxabicyclo[3.1.1]heptane as an Isostere of meta-Benzene.Angewandte Chemie (International ed. in English) · 2025Article
- Enantioselective photocatalytic synthesis of bicyclo[2.1.1]hexanes as ortho-disubstituted benzene bioisosteres with improved biological activity.Nature chemistry · 2025Article
- Expanding the Repertoire of Large Scaffolds withThe Journal of organic chemistry · 2025Article
- Article
- Three-dimensional saturated C(spNature reviews. Chemistry · 2024Review
- Germanyl triazoles as a platform for CuAAC diversification and chemoselective orthogonal cross-coupling.Beilstein journal of organic chemistry · 2024Article
- (Bio)isosteres ofBeilstein journal of organic chemistry · 2024Review
- C(spChemical science · 2023Article
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Authors and funding
10 authors.
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Abstract
Bridged or caged polycyclic hydrocarbons have rigid structures that project substituents into precise regions of 3D space, making them attractive as linking groups in materials science and as building blocks for medicinal chemistry. The efficient synthesis of new or underexplored classes of such compounds is, therefore, an important objective. Herein, we describe the silver(I)-catalyzed rearrangement of 1,4-disubstituted cubanes to cuneanes, which are strained hydrocarbons that have not received much attention since they were first described in 1970. The synthesis of 2,6-disubstituted or 1,3-disubstituted cuneanes can be achieved with high regioselectivities, with the regioselectivity being dependent on the electronic character of the cubane substituents. A preliminary assessment of cuneanes as scaffolds for medicinal chemistry suggests cuneanes could serve as isosteric replacements of
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