ArticleJournal of the American Chemical Society2021
Photochemical Formal (4 + 2)-Cycloaddition of Imine-Substituted Bicyclo[1.1.1]pentanes and Alkenes.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed.
- 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
- Collective synthesis of 1,2,4-trisubstituted, meta- and ortho-substituted arene bioisosteres from bicyclobutanes.Nature chemistry · 2026Article
- Enantioselective Synthesis of 2-Oxabicyclo[2.1.1]hexanes and Bicyclo[2.1.1]hexanes via Catalytic Asymmetric Intramolecular Photocycloadditions.Nature communications · 2026Article
- Enantioselective photocatalytic synthesis of bicyclo[2.1.1]hexanes as ortho-disubstituted benzene bioisosteres with improved biological activity.Nature chemistry · 2025Article
- Photocatalyzed Epimerization of Quaternary Stereocenters.Journal of the American Chemical Society · 2025Article
- Facile Synthesis of Housanes by an Unexpected Strategy.Journal of the American Chemical Society · 2025Article
- Enantioselective formal (3 + 3) cycloaddition of bicyclobutanes with nitrones enabled by asymmetric Lewis acid catalysis.Nature communications · 2024Article
- Three-dimensional saturated C(spNature reviews. Chemistry · 2024Review
- Article
- Programmable late-stage functionalization of bridge-substituted bicyclo[1.1.1]pentane bis-boronates.Nature chemistry · 2024Article
- (Bio)isosteres ofBeilstein journal of organic chemistry · 2024Review
- Synthesis of 2-Azanorbornanes via Strain-Release Formal Cycloadditions Initiated by Energy Transfer.Angewandte Chemie (International ed. in English) · 2023Article
- 1,2-Disubstituted bicyclo[2.1.1]hexanes as saturated bioisosteres ofChemical science · 2023Article
- Visible-light-induced [3+2] cycloadditions of donor/donor diazo intermediates with alkenes to achieve (spiro)-pyrazolines and pyrazoles.Chemical science · 2023Article
- Synthesis of polysubstituted bicyclo[2.1.1]hexanes enabling access to new chemical space.Chemical science · 2023Article
- Gram-scale synthesis of MIL-125 nanoparticles and their solution processability.Chemical science · 2023Article
- Silver(I)-Catalyzed Synthesis of Cuneanes from Cubanes and their Investigation as Isosteres.Journal of the American Chemical Society · 2023Article
- 2-Oxabicyclo[2.1.1]hexanes as saturated bioisosteres of the ortho-substituted phenyl ring.Nature chemistry · 2023Article
- Review
- Formal Cycloadditions Driven by the Homolytic Opening of Strained, Saturated Ring Systems.Angewandte Chemie (International ed. in English) · 2023Review
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4 authors.
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Abstract
Amines containing bridged bicyclic carbon skeletons are desirable building blocks for medicinal chemistry. Herein, we report the conversion of bicyclo[1.1.1]pentan-1-amines to a wide range of polysubstituted bicyclo[3.1.1]heptan-1-amines through a photochemical, formal (4 + 2)-cycloaddition of an intermediate imine diradical. To our knowledge, this is the first reported method to convert the bicyclo[1.1.1]pentane skeleton to the bicyclo[3.1.1]heptane skeleton. Hydrolysis of the imine products gives complex, sp
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