ArticleJournal of the American Chemical Society2019
Copper Hydride Catalyzed Enantioselective Synthesis of Axially Chiral 1,3-Disubstituted Allenes.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.
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Who cites it
26 citing papers in PubMed.
- Biosynthetic allene and alkyne formation by enzymatic prenyl demethylation.Nature chemical biology · 2026Article
- Biosynthetic allene and alkyne formation by enzymatic prenyl demethylation.bioRxiv : the preprint server for biology · 2026Article
- N-Heterocyclic Carbene Organocatalysis Enabled Modular Synthesis of Fluorinated Isoflavonoids to Suppress Proliferation and Migration in Breast Cancer Cells.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Synthesis of 1,3-Enynes by Iron-Catalyzed Propargylic C-H Functionalization: An Alkyne Analogue for the Eschenmoser Methenylation.Organic letters · 2024Article
- Nickel-catalysed asymmetric hydromonofluoromethylation of 1,3-enynes for enantioselective construction of monofluoromethyl-tethered chiral allenes.Chemical science · 2023Article
- Regio- and enantioselective CuH-catalyzed 1,2- and 1,4-hydrosilylation of 1,3-enynes.Nature communications · 2023Article
- Photoredox cobalt-catalyzed regio-, diastereo- and enantioselective propargylation of aldehydes via propargyl radicals.Nature communications · 2023Article
- Copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of 1,3-enynes and azomethine ylides.Nature communications · 2023Article
- A Pd-catalyzed highly selective three-component protocol for trisubstituted allenes.Chemical science · 2023Article
- Electrochemically Generated Carbanions Enable Isomerizing Allylation and Allenylation of Aldehydes with Alkenes and Alkynes.Journal of the American Chemical Society · 2023Article
- Pd/Xu-Phos-catalyzed asymmetric elimination of fully substituted enol triflates into axially chiral trisubstituted allenes.Science advances · 2023Article
- A Cascade Sonogashira Cross-Coupling-Substitution-Elimination Reaction for the Synthesis of Linear Conjugated Dienynes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Asymmetric 1,4-functionalization of 1,3-enynes via dual photoredox and chromium catalysis.Nature communications · 2022Article
- Photo and copper dual catalysis for allene syntheses from propargylic derivatives via one-electron process.Nature communications · 2022Article
- Iron-Catalyzed Contrasteric Functionalization of Allenic C(spJournal of the American Chemical Society · 2021Article
- Generation of Axially Chiral Fluoroallenes through a Copper-Catalyzed Enantioselective β-Fluoride Elimination.Journal of the American Chemical Society · 2021Article
- Decarboxylative 1,4-carbocyanation of 1,3-enynes to access tetra-substituted allenesChemical science · 2021Article
- Deciphering the Chameleonic Chemistry of Allenols: Breaking the Taboo of a Onetime Esoteric Functionality.Chemical reviews · 2021Article
- Synthesis of Aminoallenes via Selenium-π-Acid-Catalyzed Cross-Coupling ofEuropean journal of organic chemistry · 2021Article
- Palladium-catalyzed allene synthesis enabled by β-hydrogen elimination from spNature communications · 2021Article
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2 authors.
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Abstract
The general enantioselective synthesis of axially chiral disubstituted allenes from prochiral starting materials remains a long-standing challenge in organic synthesis. Here, we report an efficient enantio- and chemoselective copper hydride catalyzed semireduction of conjugated enynes to furnish 1,3-disubstituted allenes using water as the proton source. This protocol is sufficiently mild to accommodate an assortment of functional groups including keto, ester, amino, halo, and hydroxyl groups. Additionally, applications of this method for the selective synthesis of monodeuterated allenes and chiral 2,5-dihydropyrroles are described.
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