ArticleJournal of the American Chemical Society2022
One-Pot Synthesis of Strain-Release Reagents from Methyl Sulfones.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed.
- A Scalable Stereoselective Synthesis of Polysubstituted Housanes.Organic letters · 2026Article
- Stereocontrolled Synthesis of Polysubstituted Housanes viaJournal of the American Chemical Society · 2026Article
- Deuterated Cyclopropanation of Alkenes by Iron Catalysis.Organic letters · 2026Article
- Boron-Enabled Stereoselective Synthesis of Polysubstituted Housanes.Journal of the American Chemical Society · 2025Article
- Synthesis of Bicyclo[2.1.0]pentanes and Vinylcyclopropanes Using Palladium Carbenes: Ligand-Controlled Carbene Reactivity.Journal of the American Chemical Society · 2025Article
- Highly stereoselective synthesis of polysubstituted housanes and spiro-oxa-housanes: application and mechanistic insights.Chemical science · 2025Article
- Synthesis of Fused-Housane Derivatives via Intramolecular [2 + 2] Photocycloaddition.Organic letters · 2025Article
- Facile Synthesis of Housanes by an Unexpected Strategy.Journal of the American Chemical Society · 2025Article
- Strain-release trifluoromethoxylation and pentafluorosulfanoxylation of [1.1.0]bicyclobutanes: expanded access to fluorinated cyclobutane hybrid bioisosteres.Chemical communications (Cambridge, England) · 2025Article
- A reagent to access methyl sulfones.Nature communications · 2025Article
- Synthesis of 1-(phenylsulfonyl)bicyclo[1.1.0]butane from Methyl Phenyl Sulfone and Epichlorohydrin.Organic syntheses; an annual publication of satisfactory methods for the preparation of organic chemicals · 2025Article
- Visible-Light-Mediated Vicinal Dihalogenation of Unsaturated C-C Bonds Using Dual-Functional Group Transfer Reagents.Journal of the American Chemical Society · 2024Article
- Rhodium(I)-Catalyzed Annulation of Bicyclo[1.1.0]butyl-Substituted Dihydroquinolines and Dihydropyridines.Journal of the American Chemical Society · 2024Article
- Synthesis of Stereodefined Polysubstituted Bicyclo[1.1.0]butanes.Journal of the American Chemical Society · 2024Article
- Overcoming a Radical Polarity Mismatch in Strain-Release Pentafluorosulfanylation of [1.1.0]Bicyclobutanes: An Entryway to Sulfone- and Carbonyl-Containing SFAngewandte Chemie (International ed. in English) · 2024Article
- Bridge Cross-Coupling of Bicyclo[1.1.0]butanes.Organic letters · 2024Article
- One-Pot Synthesis of Difluorobicyclo[1.1.1]pentanes from α-Allyldiazoacetates.Organic letters · 2023Article
- Expedient synthesis of spiro[3.3]heptan-1-ones via strain-relocating semipinacol rearrangements.Tetrahedron · 2023Article
- Synthesis of 3-borylated cyclobutanols from epihalohydrins or epoxy alcohol derivatives.Chemical science · 2023Article
- Bicyclobutanes as unusual building blocks for complexity generation in organic synthesis.Communications chemistry · 2023Review
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Authors and funding
2 authors.
Funding
Abstract
Sulfone-substituted bicyclo[1.1.0]butanes and housanes have found widespread application in organic synthesis due to their bench stability and high reactivity in strain-releasing processes in the presence of nucleophiles or radical species. Despite their increasing utility, their preparation typically requires multiple steps in low overall yield. In this work, we report an expedient and general one-pot procedure for the synthesis of 1-sulfonylbicyclo[1.1.0]butanes from readily available methyl sulfones and inexpensive epichlorohydrin via the dialkylmagnesium-mediated formation of 3-sulfonylcyclobutanol intermediates. Furthermore, the process was extended to the formation of 1-sulfonylbicyclo[2.1.0]pentane (housane) analogues when 4-chloro-1,2-epoxybutane was used as the electrophile instead of epichlorohydrin. Both procedures could be applied on a gram scale with similar efficiency and are shown to be fully stereospecific in the case of housanes when an enantiopure epoxide was employed, leading to a streamlined access to highly valuable optically active strain-release reagents.
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Registered trials
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