ArticleJournal of the American Chemical Society2015
(4+1) vs (4+2): Catalytic Intramolecular Coupling between Cyclobutanones and Trisubstituted Allenes via C-C Activation.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 30 papers.
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Who cites it
30 citing papers in PubMed.
- Ring Expansion via Palladium-Catalyzed Aryne Insertion into C-C Bonds of Benzocyclobutenones.Angewandte Chemie (International ed. in English) · 2025Article
- Zirconium and hafnium catalyzed C-C single bond hydroboration.Nature communications · 2024Article
- Synthesis of Fluorinated Amines: A Personal Account.ACS organic & inorganic Au · 2023Review
- Unveiling the Chemistry and Synthetic Potential of Catalytic Cycloaddition Reaction of Allenes: A Review.Molecules (Basel, Switzerland) · 2023Review
- Rhodium-Catalyzed Diastereo- and Enantioselective Divergent Annulations between Cyclobutanones and 1,5-Enynes: Rapid Construction of Complex C(spJournal of the American Chemical Society · 2022Article
- Deconstructive Synthesis of Bridged and Fused Rings via Transition-Metal-Catalyzed "Cut-and-Sew" Reactions of Benzocyclobutenones and Cyclobutanones.Accounts of chemical research · 2022Article
- An endo-Directing-Group Strategy Unlocks Enantioselective (3+1+2) Carbonylative Cycloadditions of Aminocyclopropanes.Angewandte Chemie (International ed. in English) · 2022Article
- Catalytic Enantioselective Synthesis of γ-Lactams with β-Quaternary Centers via Merging of C-C Activation and Sulfonyl Radical Migration.Journal of the American Chemical Society · 2022Article
- Rhodium-Catalyzed (4+1) Cycloaddition between Benzocyclobutenones and Styrene-Type Alkenes.Angewandte Chemie (International ed. in English) · 2022Article
- Stereoselective Synthesis ofACS omega · 2021Article
- Regioselective activation of benzocyclobutenones and dienamides lead to anti-Bredt bridged-ring systems by a [4+4] cycloaddition.Nature communications · 2021Article
- Conversion of anilines to chiral benzylic amines via formal one-carbon insertion into aromatic C-N bonds.Nature communications · 2020Article
- Enantioselective Type II Cycloaddition of Alkynes via C-C Activation of Cyclobutanones: Rapid and Asymmetric Construction of [3.3.1] Bridged Bicycles.Journal of the American Chemical Society · 2020Article
- Palladium-catalyzed hydroalkylation of methylenecyclopropanes with simple hydrazones.Chemical science · 2020Article
- Enantioselective Desymmetrization of Cyclobutanones: A Speedway to Molecular Complexity.Angewandte Chemie (International ed. in English) · 2020Review
- Nickel-Catalyzed Asymmetric Domino Ring Opening/Cross-Coupling Reaction of Cyclobutanones via a Reductive Strategy.iScience · 2020Article
- Kinetic Resolution via Rh-Catalyzed C-C Activation of Cyclobutanones at Room Temperature.Journal of the American Chemical Society · 2019Article
- Enantioselective palladium/copper-catalyzed C-C σ-bond activation synergized with Sonogashira-type C(spChemical science · 2019Article
- Concise Synthesis of (-)-Cycloclavine and (-)-5- epi-Cycloclavine via Asymmetric C-C Activation.Journal of the American Chemical Society · 2018Article
- Fused-Ring Formation by an Intramolecular "Cut-and-Sew" Reaction between Cyclobutanones and Alkynes.Angewandte Chemie (International ed. in English) · 2018Article
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Authors and funding
2 authors.
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Abstract
Herein we describe a rhodium-catalyzed (4+1) cyclization between cyclobutanones and allenes, which provides a distinct [4.2.1]-bicyclic skeleton containing two quaternary carbon centers. The reaction involves C-C activation of cyclobutanones and employs allenes as a one-carbon unit. A variety of functional groups can be tolerated, and a diverse range of polycyclic scaffolds can be accessed. Excellent enantioselectivity can be obtained, which is enabled by a TADDOL-derived phosphoramidite ligand. The bridged bicyclic products can be further functionalized or derivatized though simple transformations.
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