ArticleNature communications2021
Direct access to spirocycles by Pd/WingPhos-catalyzed enantioselective cycloaddition of 1,3-enynes.
Article in Nature communications, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed.
- Cobalt-Catalyzed Reductive Asymmetric Dimerization of 1,3-Enynes: Rapid Synthesis of Enantioenriched Skipped 1,3,6-Trienes.Angewandte Chemie (International ed. in English) · 2026Article
- Catalytic Asymmetric Spiroannulation to Access Polycyclic Spiro Enones via Transient Axial-to-Point Chirality Induction and Transfer.Nature communications · 2026Article
- Alcohol-Directed Carboamination of Conjugated Enynes.Angewandte Chemie (International ed. in English) · 2026Article
- Alkyne migratory functionalization via C(spNature communications · 2026Article
- Chemodivergent Coupling of 1,3-Enynes with Anilines to Access Dihydropyrrole Skeleton under Palladium Catalysis.Nature communications · 2026Article
- Catalytic asymmetric synthesis of (N, N)- spiroketal via Pd-catalyzed enantioconvergent aminocarbonylation and dearomative nucleophilic aza-addition.Nature communications · 2025Article
- Dynamic radical recombination enabling stereodivergent construction of spirocycles with nonadjacent stereocenters.Nature communications · 2025Article
- Dual-Ligand Strategy in Rh-Catalyzed Sequential Hydrofunctionalization of Valylene.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Recent Advancements in the Cyclization Strategies of 1,3-Enynes Towards the Synthesis of Heterocyclic/Carbocyclic Frameworks.Chemistry, an Asian journal · 2025Review
- Multimodal Precise Control Over Multiselective Carbonylation of 1,3-Enynes.Journal of the American Chemical Society · 2025Article
- Preparation of Benzo[The Journal of organic chemistry · 2024Article
- Escape from Hydrofunctionalization: Palladium Hydride-Enabled Difunctionalization of Conjugated Dienes and Enynes.Angewandte Chemie (International ed. in English) · 2023Article
- Nickel-catalysed asymmetric hydromonofluoromethylation of 1,3-enynes for enantioselective construction of monofluoromethyl-tethered chiral allenes.Chemical science · 2023Article
- Chemodivergence in Pd-catalyzed desymmetrization of allenes: enantioselective [4+3] cycloaddition, desymmetric allenylic substitution and enynylation.Chemical science · 2023Article
- Asymmetric formal spNature communications · 2023Article
- Donor-Acceptor Cyclopropanes: Activation Enabled by a Single, Vinylogous Acceptor.Angewandte Chemie (International ed. in English) · 2023Article
- Catalytic Enantioselective Synthesis of α-Difunctionalized Cyclic Sulfones.The Journal of organic chemistry · 2022Article
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Authors and funding
9 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Spirocycles play an important role in drug discovery and development. The direct, catalytic, and enantioselective synthesis of spirocycles from readily available starting materials and in an atom economic manner remains a highly sought-after task in organic synthesis. Herein, an enantioselective Pd-hydride-catalyzed cycloaddition method for the synthesis of spirocyclic compounds directly from two classes of commonly available starting materials, 1,3-enynes and cyclic carbon-hydrogen (C-H) bonds, is reported. The reactions employ a chiral Pd/WingPhos catalyst to both suppress the formation of bis-allenyl by-products and control the stereoselectivity. 1,3-Enynes are used as dielectrophilic four-carbon units in the cycloaddition reactions, which also enables an enyne substrate-directed enantioselectivity switch with good levels of stereocontrol. The present spirocycle synthesis tolerates a broad range of functional groups of 1,3-enyne substrates, including alcohols, esters, nitriles, halides, and olefins. A variety of diverse cyclic nucleophiles, including pharmaceutically important heterocycles and carbocycles, can be flexibly incorporated with spiro scaffolds.
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