ArticleAngewandte Chemie (International ed. in English)2022
Enantio- and Diastereoselective Copper-Catalyzed Allylboration of Alkynes with Allylic gem-Dichlorides.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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11 citing papers in PubMed.
- Inductive Diastereoselective Rationale for a Catalytic Strategy to Build Densely Chiral Five-Membered Carbocycles.JACS Au · 2026Article
- Enantioselective synthesis of allylic boronates bearing a stereodefined (Organic chemistry frontiers : an international journal of organic chemistry · 2026Article
- Catalytic Asymmetric 1,2-Migration/Allylation of Alkynyl Boronate Complexes: A Modular Route to Enantioenriched Skipped 1,4-Dienes.Journal of the American Chemical Society · 2026Article
- Synthesis and applications of alkenyl chlorides (vinyl chlorides): a review.Beilstein journal of organic chemistry · 2026Review
- Design Approaches That Utilize Ionic Interactions to Control Selectivity in Transition Metal Catalysis.Chemical reviews · 2025Review
- Cu-Bpin-mediated dimerization of 4,4-dichloro-2-butenoic acid derivatives enables the synthesis of densely functionalized cyclopropanes.Beilstein journal of organic chemistry · 2025Article
- Copper-catalyzed asymmetric allylic substitution of racemic/Chemical science · 2024Review
- Catalytic Alkyne Allylboration: A Quest for Selectivity.ACS catalysis · 2023Review
- Copper-Catalyzed Enantioselective Borylative Allyl-Allyl Coupling of Allenes and AllylicACS catalysis · 2023Article
- Updated Progress of the Copper-Catalyzed Borylative Functionalization of Unsaturated Molecules.Molecules (Basel, Switzerland) · 2023Review
- Enantio- and Diastereoselective Copper-Catalyzed Allylboration of Alkynes with Allylic gem-Dichlorides.Angewandte Chemie (International ed. in English) · 2022Article
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3 authors.
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Abstract
Allylic gem-dichlorides are shown to be efficient substrates for catalytic asymmetric allylboration of alkynes. The method employs a chiral NHC-Cu catalyst capable of generating in a single step chiral skipped dienes bearing a Z-alkenyl chloride, a trisubstituted E-alkenyl boronate and a bis-allylic stereocenter with excellent levels of chemo-, regio- enantio- and diastereoselectivity. This high degree of functionalization makes these products versatile building blocks as illustrated with the synthesis of several optically active compounds. DFT calculations support the key presence of a metal cation bridge ligand-substrate interaction and account for the stereoselectivity outcome.
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