ArticleNature chemistry2021
A catalytic asymmetric cross-coupling approach to the synthesis of cyclobutanes.
Article in Nature chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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18 citing papers in PubMed, 77 citations in OpenAlex.
- Catalytic Transformations of Aza-Cyclobutenes, Fused Cyclobutenes, and Cyclobutenones.Chemical record (New York, N.Y.) · 2026Review
- Modular diastereoselective synthesis of hindered cyclobutane amino nitriles through triplet nitrene-mediated ring expansion.Nature chemistry · 2026Article
- Alkyne migratory functionalization via C(spNature communications · 2026Article
- Ligand-controlled divergent enantioselective hydroarylation of cyclobutenes.Chemical science · 2025Article
- Diastereoselective synthesis of multi-substituted cyclobutanes via catalyst-controlled regiodivergent hydrophosphination of acyl bicyclobutanes.Nature communications · 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
- Asymmetric synthesis of atropisomers featuring cyclobutane boronic esters facilitated by ring-strained B-ate complexes.Nature communications · 2024Article
- Rh(I)-Catalyzed Regio- and Enantioselective Ring Opening of Vinyl Cyclopropanes.Journal of the American Chemical Society · 2024Article
- Photochemical α-selective radical ring-opening reactions of 1,3-disubstituted acyl bicyclobutanes with alkyl halides: modular access to functionalized cyclobutenes.Chemical science · 2023Article
- C(spChemical science · 2023Article
- Enantioselective [3+2]-cycloaddition of 2,3-disubstituted cyclobutenones: vicinal quaternary stereocenters construction and skeletal functionalization.Chemical science · 2023Article
- A general catalytic synthetic strategy for highly strained methylenecyclobutanes and spiromethylenecyclobutanes.Chemical science · 2023Article
- Catalytic Enantioselective Synthesis of 3-Piperidines from Arylboronic Acids and Pyridine.Journal of the American Chemical Society · 2023Article
- Rhodium-Catalyzed Asymmetric Arylation of Cyclobutenone Ketals.Angewandte Chemie (International ed. in English) · 2023Article
- Catalytic asymmetric hydrometallation of cyclobutenes with salicylaldehydes.Chemical science · 2021Article
- Catalytic Arylboration of Spirocyclic Cyclobutenes: Rapid Access to Highly Substituted Spiro[3.n]alkanes.ACS catalysis · 2021Article
- Regioselective Monoborylation of Spirocyclobutenes.Organic letters · 2021Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Stereodefined four-membered rings are common motifs in bioactive molecules and versatile intermediates in organic synthesis. However, the synthesis of complex, chiral cyclobutanes is a largely unsolved problem and there is a need for general and modular synthetic methods. Here we report a series of asymmetric cross-coupling reactions between cyclobutenes and arylboronic acids which are initiated by Rh-catalysed asymmetric carbometallation. After the initial carborhodation, Rh-cyclobutyl intermediates undergo chain-walking or C-H insertion so that overall a variety of additions such as reductive Heck reactions, 1,5-addition and homoallylic substitution are observed. The synthetic applicability of these highly stereoselective transformations is demonstrated in the concise syntheses of the drug candidates Belaperidone and PF-04862853. We anticipate this approach will be widely adopted by synthetic and medicinal chemists. While the carbometallation approach reported here is exemplified with Rh and arylboronic acids, it is likely to be applicable to other metals and nucleophiles.
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