ArticleJournal of the American Chemical Society2020
Enantioselective Type II Cycloaddition of Alkynes via C-C Activation of Cyclobutanones: Rapid and Asymmetric Construction of [3.3.1] Bridged Bicycles.
Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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14 citing papers in PubMed, 59 citations in OpenAlex.
- Catalytic asymmetric tandem Heck/Sonogashira reaction enabling access to versatile chiral bridged ring scaffolds.Nature communications · 2025Article
- "Cut-and-Sew" Reactions of β-Lactams via C-C Bond Activation.Journal of the American Chemical Society · 2025Article
- Switchable organocatalytic enantioselective sulfenocyclization of cyclohexadienes enabling chemodivergent access to chiral bicyclo[m.n.1] ring systems.Nature communications · 2025Article
- Ring Expansion via Palladium-Catalyzed Aryne Insertion into C-C Bonds of Benzocyclobutenones.Angewandte Chemie (International ed. in English) · 2025Article
- Palladium-catalyzed selective C-C bond cleavage of keto-vinylidenecyclopropanes: construction of structurally rich dihydrofurans and tetrahydrofurans.Chemical science · 2024Article
- Zirconium and hafnium catalyzed C-C single bond hydroboration.Nature communications · 2024Article
- Enantioselective Total Synthesis of (-)-Himalensine A via a Palladium and 4-Hydroxyproline Co-catalyzed Desymmetrization of Vinyl-bromide-tethered Cyclohexanones.Journal of the American Chemical Society · 2023Article
- 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
- Rh(i)-catalyzed dimerization of ene-vinylidenecyclopropanes for the construction of spiro[4,5]decanes and mechanistic studies.Chemical science · 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
- Intermolecular [5+2] Annulation between 1-Indanones and Internal Alkynes by Rhodium-Catalyzed C-C Activation.Angewandte Chemie (International ed. in English) · 2021Article
- Facile generation of bridged medium-sized polycyclic systems by rhodium-catalysed intramolecular (3+2) dipolar cycloadditions.Nature communications · 2021Article
- Regioselective activation of benzocyclobutenones and dienamides lead to anti-Bredt bridged-ring systems by a [4+4] cycloaddition.Nature communications · 2021Article
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7 authors at 1 institution in 1 country.
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Abstract
Synthesis of bridged scaffolds via Type II cyclization constitutes substantial challenges due to the intrinsic ring strain accumulated in reaction transition states. Catalytic enantioselective Type II-cyclization methods are even rarer. Here, we describe a detailed study of developing a Rh(I)-catalyzed enantioselective intramolecular Type II cyclization of alkynes via C-C activation of cyclobutanones. This method offers a rapid approach to access a wide range of functionalized [3.3.1]-bridged bicycles along with an exocyclic olefin and an all-carbon quaternary stereocenter. Excellent enantioselectivity has been achieved using a combination of cationic rhodium(I) and DTBM-segphos. Attributed to the redox neutral and strong acid/base-free reaction conditions, high chemoselectivity has also been observed. For the oxygen-tethered substrates, the reaction can proceed at room temperature. In addition, partial kinetic resolution has been achieved for substrates with existing stereocenters, forging interesting chiral tricyclic scaffolds. The methylalkyne-derived substrates gave unexpected dimeric structures in good yield with excellent enantioselectivity and complete diastereoselectivity. Furthermore, the bridged bicyclic products can be diversely functionalized through simple transformations. Finally, mechanistic studies reveal a surprising reaction pathway that involves forming a metal-stabilized
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