ArticleAngewandte Chemie (International ed. in English)2014
Enantioselective copper-catalyzed carboetherification of unactivated alkenes.
Article in Angewandte Chemie (International ed. in English), 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed.
- Copper-catalyzed enantioselective synthesis of γ-butenolides via radical diversification of allenoic acid.Nature communications · 2025Article
- Copper-Catalyzed Cyclization and Alkene Transposition Cascade Enables a Modular Synthesis of Complex Spirocyclic Ethers.Journal of the American Chemical Society · 2025Article
- Mechanistic study on the side arm effect in a palladium/Xu-Phos-catalyzed enantioselective alkoxyalkenylation of γ-hydroxyalkenes.Nature communications · 2023Article
- Copper-Catalyzed Enantioselective Aerobic Alkene Aminooxygenation and Dioxygenation: Access to 2-Formyl Saturated Heterocycles and Unnatural Proline Derivatives.Journal of the American Chemical Society · 2023Article
- Photoinduced β-fragmentation of aliphatic alcohol derivatives for forging C-C bonds.Nature communications · 2022Article
- Copper-Catalyzed Enantioselective Oxysulfenylation of Alkenols: Synthesis of Arylthiomethyl-Substituted Cyclic Ethers.ACS catalysis · 2022Article
- Asymmetric radical carboesterification of dienes.Nature communications · 2021Article
- Copper-catalyzed enantioselective alkene carboetherification for the synthesis of saturated six-membered cyclic ethers.Chemical communications (Cambridge, England) · 2021Article
- Copper-catalyzed enantioselective synthesis of bridged bicyclic ketals from 1,1-disubstituted-4-methylene-1,6-hexanediols and related alkenols.Chemical communications (Cambridge, England) · 2021Article
- Catalytic generation of alkoxy radicals from unfunctionalized alcohols.Chemical science · 2020Review
- Copper-Catalyzed Enantioselective Hydroalkoxylation of Alkenols for the Synthesis of Cyclic Ethers.Organic letters · 2020Article
- Enantioselective, Aerobic Copper-Catalyzed Intramolecular Carboamination and Carboetherification of Unactivated Alkenes.ACS catalysis · 2020Article
- Catalytic enantioselective oxidative coupling of saturated ethers with carboxylic acid derivatives.Nature communications · 2019Article
- Synthesis of Phthalans Via Copper-Catalyzed Enantioselective Cyclization/Carboetherification of 2-Vinylbenzyl Alcohols.Organic letters · 2018Article
- Synthesis of Spirocyclic Ethers by Enantioselective Copper-Catalyzed Carboetherification of Alkenols.Angewandte Chemie (International ed. in English) · 2018Article
- Selenide-catalyzed enantioselective synthesis of trifluoromethylthiolated tetrahydronaphthalenes by merging desymmetrization and trifluoromethylthiolation.Nature communications · 2018Article
- Stereoselective and Regioselective Synthesis of Heterocycles via Copper-Catalyzed Additions of Amine Derivatives and Alcohols to Alkenes.The Journal of organic chemistry · 2017Article
- Direct Synthesis of 2-Formylpyrrolidines, 2-Pyrrolidinones and 2-Dihydrofuranones via Aerobic Copper-Catalyzed Aminooxygenation and Dioxygenation of 4-Pentenylsulfonamides and 4-Pentenylalcohols.Journal of the American Chemical Society · 2017Article
- Development of Enantioselective Palladium-Catalyzed Alkene Carboalkoxylation Reactions for the Synthesis of Tetrahydrofurans.Angewandte Chemie (International ed. in English) · 2015Article
- Versatile Enantioselective Synthesis of Functionalized Lactones via Copper-Catalyzed Radical Oxyfunctionalization of Alkenes.Journal of the American Chemical Society · 2015Article
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7 authors.
Funding
Abstract
Chiral saturated oxygen heterocycles are important components of bioactive compounds. Cyclization of alcohols onto pendant alkenes is a direct route to their synthesis, but few catalytic enantioselective methods enabling cyclization onto unactivated alkenes exist. Herein reported is a highly efficient copper-catalyzed cyclization of γ-unsaturated pentenols which terminates in C-C bond formation, a net alkene carboetherification. Both intra- and intermolecular C-C bond formations are demonstrated, thus yielding functionalized chiral tetrahydrofurans as well as fused-ring and bridged-ring oxabicyclic products. Transition-state calculations support a cis-oxycupration stereochemistry-determining step.
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