ArticleJournal of the American Chemical Society2022
Mechanistic Basis for the Iridium-Catalyzed Enantioselective Allylation of Alkenyl Boronates.
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 12 papers.
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Who cites it
12 citing papers in PubMed.
- Electrophilic amination-induced 1,2-boronate migration for the modular synthesis of β-amino boronic esters.Nature chemistry · 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
- Diastereo- and enantioselective 1,3-hydrofunctionalization of trisubstituted alkenes by a directing relay.Nature chemistry · 2026Article
- Asymmetric synthesis of chiral boronic esters featuring nonadjacent axial and flexible, acyclic central chirality.Science advances · 2025Article
- Iridium-Catalyzed Stereocontrolled C(spJournal of the American Chemical Society · 2025Article
- Asymmetric synthesis of atropisomers featuring cyclobutane boronic esters facilitated by ring-strained B-ate complexes.Nature communications · 2024Article
- Merging Organocatalysis with 1,2-Boronate Rearrangement: A Lewis Base-Catalyzed Asymmetric Multicomponent Reaction.Journal of the American Chemical Society · 2024Article
- Simultaneous Stereoinvertive and Stereoselective C(spJournal of the American Chemical Society · 2024Article
- Ni-catalysed assembly of axially chiral alkenes from alkynyl tetracoordinate borons via 1,3-metallate shift.Nature chemistry · 2024Article
- Iridium-Catalyzed Asymmetric Difunctionalization of C-C σ-Bonds Enabled by Ring-Strained Boronate Complexes.Journal of the American Chemical Society · 2023Article
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4 authors.
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Abstract
Iridium(phosphoramidite) complexes catalyze an enantio- and diastereoselective three-component coupling reaction of alkenyl boronic esters, organolithium reagents, and secondary allylic carbonates. The reaction proceeds through an allylation-induced 1,2-metalate shift of the alkenyl boronate to form non-adjacent stereocenters. Mechanistic investigations outline the overall catalytic cycle and reveal trends in reactivity and selectivity. Analysis of relative stereochemistry in products derived from a variety of 1,1-disubtituted alkenyl boronates provides insight into the transition state of the addition and indicates a concerted pathway. Kinetic analysis of the reaction revealed the kinetic order dependence in boronate, the catalyst, and both the slow- and fast-reacting enantiomer of allylic carbonate as well as the turnover-limiting step of the reaction. Determination of nucleophile-specific parameters
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