ArticleThe Journal of organic chemistry2025
Central-to-Axial-to-Central Chirality Transfer in the Au(I)-Catalyzed Cycloisomerization of Propargyl Vinyl Ethers to Cyclopentadienes.
Article in The Journal of organic chemistry, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.
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1 citing paper in PubMed.
- Enantioselective Synthesis of a New Class of Stable and Functionalized Cyclopentadienes via CuH-Catalysis.Angewandte Chemie (International ed. in English) · 2026Article
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5 authors.
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Abstract
An easy approach to the enantioselective synthesis of five-, six-, and seven-membered ring-fused cyclopentadienes (85-99% ee) is based on the Au(I)-catalyzed cycloisomerization of enantiomerically pure or enriched propargyl vinyl ethers, which occurs with complete central-to-axial-to-central chirality transfer. DFT calculations show that the formation of a nonplanar σ-Au(I)-pentadienyl cation intermediate having a helical configuration, which quickly cyclizes to form the target cyclopentadiene, accounts for the lack of erosion of the initial optical purity. From a synthetic point of view, when the cyclopentadienes are subjected to a quick 1,5-
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