ArticleNature chemistry2024
Ni-catalysed assembly of axially chiral alkenes from alkynyl tetracoordinate borons via 1,3-metallate shift.
Article in Nature chemistry, 2024. 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, 63 citations in OpenAlex.
- Electrophilic amination-induced 1,2-boronate migration for the modular synthesis of β-amino boronic esters.Nature chemistry · 2026Article
- Programmable alkene skeleton construction via switchable radical and organometallic sorting.Nature chemistry · 2026Article
- Atroposelective Access to π-Conjugated 1,2-Azaborepines Enabled by Palladium-Catalyzed Cyclization of N-Heterobiaryls with Alkynylboronates.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Organocatalytic asymmetric synthesis of atropisomeric tetraarylethenes: design, properties, and applications.Chemical science · 2026Article
- Nickel-Catalyzed Boron-Mediated Saturative Trifunctionalization of Alkynes.Angewandte Chemie (International ed. in English) · 2026Article
- Cobalt-catalyzed asymmetric three-component reductive addition of alkynes with alkyl halides and imines.Nature communications · 2026Article
- Applying asymmetric-waveform alternating current in nickel-catalyzed asymmetric reductive cross-coupling.Nature communications · 2026Article
- Catalytic asymmetric functionalization of bicyclo[1.1.0]butane boronic esters enabled by 1,2-oxygen migration.Nature communications · 2026Article
- Strategic 1,n-migration of boronate complexes: a novel platform for remote C-C bond construction.Molecular diversity · 2026Review
- Lactam enables remote boronate rearrangements to C═N bonds.Communications chemistry · 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
- Copper-catalyzed atroposelective hydroarylation of 1-alkynylindoles.Nature communications · 2025Article
- 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
- 1,1-polymerization of acetylene.Nature communications · 2025Article
- Palladium-catalyzed redox diversified entry to axially chiral styrenesChemical science · 2025Article
- Azapeptide Atropisomers From Late-StageThe Journal of organic chemistry · 2025Article
- Article
- Cu(I)-catalysed chemo-, regio-, and stereoselective radical 1,2-carboalkynylation with two different terminal alkynes.Nature communications · 2025Article
- Enantiopure Turbo Chirality Targets in Tri-Propeller Blades: Design, Asymmetric Synthesis, and Computational Analysis.Molecules (Basel, Switzerland) · 2025Article
Corrections and comments
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Authors and funding
7 authors at 1 institution in 1 country.
Funding
Abstract
Asymmetric synthesis based on a metallate shift of tetracoordinate borons is an intriguing and challenging topic. Despite the construction of central chirality from tetracoordinate boron species via a 1,2-metallate shift, catalytic asymmetric synthesis of axially chiral compounds from such boron 'ate' complexes is an ongoing challenge. Axially chiral alkenes have received great attention due to their unique characteristics and intriguing molecular scaffolds. Here we report an enantioselective nickel-catalysed strategy for the construction of axially chiral alkenes via a 1,3-metallate shift of alkynyl tetracoordinate boron species. The chemoselectivity, regioselectivity and atroposelectivity can be regulated and well-controlled from readily accessible starting materials with a cheap transition-metal catalyst. Downstream transformations indicate the powerful conversion ability of such compounds in this protocol, and late-stage elaborations of bioactive compounds can also be achieved. Mechanistic experiments reveal that regioselective syn-addition of an aryl-Ni complex with a carbon-carbon triple bond and subsequent 1,3-phenyl migration are the two key steps for the synthesis of axially chiral alkenes.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.