ArticleJournal of the American Chemical Society2023
Iridium-Catalyzed Asymmetric Difunctionalization of C-C σ-Bonds Enabled by Ring-Strained Boronate Complexes.
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 26 papers.
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Who cites it
26 citing papers in PubMed.
- A de-novo Approach Towards Divergent [3+2π/σ] Photocycloadditions of Nitrones via Assembly-Controlled Kinetic Electron Transfer Gating.Angewandte Chemie (International ed. in English) · 2026Article
- Article
- Recent Progress in Coupling Reactions Involving the Novel Substrate of Bicyclo[1.1.0]butane (BCB).Topics in current chemistry (Cham) · 2026Review
- Harnessing Molecular Strain to Program 1,2-Migration in Boronic Ester Chemistry.Chemistry, an Asian journal · 2026Review
- Stereodivergent Access to Aliphatic Nitro Compounds Bearing Multi-Contiguous Stereocenters via Sequential Catalysis.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Catalytic asymmetric functionalization of bicyclo[1.1.0]butane boronic esters enabled by 1,2-oxygen migration.Nature communications · 2026Article
- Strain-Release Induced 1,2-Metallate Rearrangement of Geminal Diborons: Multicomponent 1,5-Difunctionalization via Ring-Opening Coupling.Angewandte Chemie (International ed. in English) · 2026Article
- Catalytic Asymmetric 1,2-Migration/Allylation of Alkynyl Boronate Complexes: A Modular Route to Enantioenriched Skipped 1,4-Dienes.Journal of the American Chemical Society · 2026Article
- Enantioselective Trifunctionalization of Terminal Alkynes.Journal of the American Chemical Society · 2025Article
- Asymmetric synthesis of chiral boronic esters featuring nonadjacent axial and flexible, acyclic central chirality.Science advances · 2025Article
- Article
- Polycyclic Scaffolds through the Intermediacy of Boron-Stabilized Nonclassical Carbocations.Journal of the American Chemical Society · 2025Article
- Fused-Linked and Spiro-Linked N-Containing Heterocycles.International journal of molecular sciences · 2025Review
- Cu-Catalyzed Chemoselective Borylcupration of Borylated (ACS catalysis · 2025Article
- Diastereoselective synthesis of multi-substituted cyclobutanes via catalyst-controlled regiodivergent hydrophosphination of acyl bicyclobutanes.Nature communications · 2025Article
- Regiodivergent hydrophosphination of Bicyclo[1.1.0]-Butanes under catalyst control.Nature communications · 2025Article
- Borylated strain rings synthesis via photorearrangements enabled by energy transfer catalysis.Nature communications · 2025Article
- Generation and Use of Bicyclo[1.1.0]butyllithium under Continuous Flow Conditions.Organic letters · 2025Article
- Facile Synthesis of Housanes by an Unexpected Strategy.Journal of the American Chemical Society · 2025Article
- Difunctionalization of bicyclo[1.1.0]butanes enabled by merging C-C cleavage and ruthenium-catalysed remote C-H activation.Nature synthesis · 2025Article
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Authors and funding
7 authors.
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Abstract
Enantioenriched organoboron intermediates are important building blocks in organic synthesis and drug discovery. Recently, transition metal-catalyzed enantioselective 1,2-metalate rearrangements of alkenylboronates have emerged as an attractive protocol to access these valuable reagents by installing two different carbon fragments across C═C π-bonds. Herein, we report the development of an iridium-catalyzed asymmetric allylation-induced 1,2-metalate rearrangement of bicyclo[1.1.0]butyl (BCB) boronate complexes enabled by strain release, which allows asymmetric difunctionalization of C-C σ-bonds, including dicarbonation and carboboration. This protocol provides a variety of enantioenriched three-dimensional 1,1,3-trisubstituted cyclobutane products bearing a boronic ester that can be readily derivatized. Notably, the reaction gives
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Registered trials
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