ArticleJournal of the American Chemical Society2019
Catalytic Enantioselective Synthesis of Cyclobutenes from Alkynes and Alkenyl Derivatives.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 34 papers.
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Who cites it
34 citing papers in PubMed, 120 citations in OpenAlex.
- Single-carbon insertion enables conversion of cyclopropenes into cyclobutenes: access to oxaspiro[2.3]hexenes.Chemical science · 2026Article
- Phosphine-Catalyzed Unsymmetric [2 + 2] Annulation of Allenyl Phosphonates for Highly Substituted Cyclobutenes.Angewandte Chemie (International ed. in English) · 2026Article
- Catalytic Transformations of Aza-Cyclobutenes, Fused Cyclobutenes, and Cyclobutenones.Chemical record (New York, N.Y.) · 2026Review
- Reenvisioning the De Mayo Reaction: A Boron-Enabled Cycloaddition Approach.Angewandte Chemie (International ed. in English) · 2026Article
- Catalytic Enantioselective Elimination of Cyclobutanols.Journal of the American Chemical Society · 2026Article
- Ligand Effects in Regio- and Enantioselective Cobalt-Catalyzed Intramolecular [4+2]- and [2+2]-Cycloaddition Reactions of Unactivated 1,3-Diene-8-ynes and 1,3-Diene-8-enes.Angewandte Chemie (International ed. in English) · 2025Article
- Pathway-divergent coupling of alkynes and cyclobutenes through enantioselective cobalt catalysis.Nature communications · 2025Article
- Photoredox cobalt-catalyzed asymmetric desymmetric reductive coupling of cyclobutenes with alkynes.Nature communications · 2025Article
- Palladium-Catalyzed Site-Selective Regiodivergent Carbocyclization of Di- and Trienallenes: A Switch between Substituted Cyclohexene and Cyclobutene.Journal of the American Chemical Society · 2025Article
- Unveiling the Use of 1,1-Bis(triflyl)ethylene as CFOrganic letters · 2024Article
- Pathway-divergent coupling of 1,3-enynes with acrylates through cascade cobalt catalysis.Nature communications · 2024Article
- Chemoenzymatic synthesis of optically active α-cyclopropyl-pyruvates and cyclobutenoates via enzyme-catalyzed carbene transfer with diazopyruvate.Organic chemistry frontiers : an international journal of organic chemistry · 2024Article
- Cobalt-Catalyzed Enantioselective Hydroboration of α-Substituted Acrylates.Journal of the American Chemical Society · 2024Article
- Borylated cyclobutanesChemical science · 2024Article
- Strain-Inducing Positional Alkene Isomerization.Journal of the American Chemical Society · 2023Article
- Ethene-1,1-disulfonyl Difluoride (EDSF) for SuFEx Click Chemistry: Synthesis of SuFExable 1,1-Bissulfonylfluoride Substituted Cyclobutene Hubs.Angewandte Chemie (International ed. in English) · 2023Article
- Chemodivergent, Regio- and Enantioselective Cycloaddition Reactions between 1,3-Dienes and Alkynes.Angewandte Chemie (International ed. in English) · 2023Article
- Synthesis of 3-borylated cyclobutanols from epihalohydrins or epoxy alcohol derivatives.Chemical science · 2023Article
- Boronic Ester Enabled [2 + 2]-Cycloadditions by Temporary Coordination: Synthesis of Artochamin J and Piperarborenine B.Journal of the American Chemical Society · 2022Article
- Copper-catalyzed radical cascade reaction of simple cyclobutanes: synthesis of highly functionalized cyclobutene derivatives.Chemical science · 2022Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Discovery of enantioselective catalytic reactions for the preparation of chiral compounds from readily available precursors, using scalable and environmentally benign chemistry, can greatly impact their design, synthesis, and eventually manufacture on scale. Functionalized cyclobutanes and cyclobutenes are important structural motifs seen in many bioactive natural products and pharmaceutically relevant small molecules. They are also useful precursors for other classes of organic compounds such as other cycloalkane derivatives, heterocyclic compounds, stereodefined 1,3-dienes, and ligands for catalytic asymmetric synthesis. The simplest approach to make cyclobutenes is through an enantioselective [2 + 2]-cycloaddition between an alkyne and an alkenyl derivative, a reaction which has a long history. Yet known reactions of this class that give acceptable enantioselectivities are of very narrow scope and are strictly limited to activated alkynes and highly reactive alkenes. Here, we disclose a broadly applicable enantioselective [2 + 2]-cycloaddition between wide variety of alkynes and alkenyl derivatives, two of the most abundant classes of organic precursors. The key cycloaddition reaction employs catalysts derived from readily synthesized ligands and an earth-abundant metal, cobalt. Over 50 different cyclobutenes with enantioselectivities in the range of 86-97% ee are documented. With the diverse functional groups present in these compounds, further diastereoselective transformations are easily envisaged for synthesis of highly functionalized cyclobutanes and cyclobutenes. Some of the novel observations made during these studies including a key role of a cationic Co(I)-intermediate, ligand and counterion effects on the reactions, can be expected to have broad implications in homogeneous catalysis beyond the highly valuable synthetic intermediates that are accessible by this route.
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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.