ArticleNature communications2019
Catalytic enantioselective construction of axial chirality in 1,3-disubstituted allenes.
Article in Nature communications, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 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
- Enantioselective homocoupling of allenylic alcohols through divergent cooperative catalysis.Chemical science · 2025Article
- P-stereogenic centre via Pd/Cu-bimetallic catalytic selective phosphinylation of allenylic acetates.Nature communications · 2025Article
- Iridium-Catalyzed Asymmetric Allenylic Substitution via Kinetic Resolution Enabled by New Monodentate Ligands.Angewandte Chemie (International ed. in English) · 2025Article
- Cross-coupling of organic fluorides with allenes: a silyl-radical-relay pathway for the construction of α-alkynyl-substituted all-carbon quaternary centres.Chemical science · 2024Article
- Chemodivergence in Pd-catalyzed desymmetrization of allenes: enantioselective [4+3] cycloaddition, desymmetric allenylic substitution and enynylation.Chemical science · 2023Article
- A Pd-catalyzed highly selective three-component protocol for trisubstituted allenes.Chemical science · 2023Article
- Palladium-catalyzed asymmetric allenylic alkylation: construction of multiple chiral thiochromanone derivatives.Chemical science · 2023Article
- Asymmetric α-allylic allenylation of β-ketocarbonyls and aldehydes by synergistic Pd/chiral primary amine catalysis.Nature communications · 2023Article
- Palladium-Catalyzed Stereoselective Construction of 1,3-Stereocenters Displaying Axial and Central Chirality via Asymmetric Alkylations.Molecules (Basel, Switzerland) · 2023Article
- Photo and copper dual catalysis for allene syntheses from propargylic derivatives via one-electron process.Nature communications · 2022Article
- Chirality memory of α-methylene-π-allyl iridium species.Chemical science · 2021Article
- A palladium-catalyzed approach to allenic aromatic ethers and first total synthesis of terricollene A.Chemical science · 2021Article
- Deciphering the Chameleonic Chemistry of Allenols: Breaking the Taboo of a Onetime Esoteric Functionality.Chemical reviews · 2021Article
- Palladium-catalyzed allene synthesis enabled by β-hydrogen elimination from spNature communications · 2021Article
- Mechanistic Aspects and Synthetic Applications of Radical Additions to Allenes.Chemical reviews · 2019Article
- Copper Hydride Catalyzed Enantioselective Synthesis of Axially Chiral 1,3-Disubstituted Allenes.Journal of the American Chemical Society · 2019Article
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Authors and funding
4 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Metal-catalyzed enantioselective construction of the loosening axial allene chirality spreading over three carbon atoms using a chiral ligand is still a significant challenge. In the literature, steric effect of the substrates is the major strategy applied for such a purpose. Herein, we present a general palladium-catalyzed asymmetrization of readily available racemic 2,3-allenylic carbonates with different types of non-substituted and 2-substituted malonates using (R)-(-)-DTBM-SEGPHOS as the preferred ligand to afford 1,3-disubstituted chiral allenes with 90~96% ee. This protocol has been applied to the first enantioselective synthesis of natural product, (R)-traumatic lactone. Control experiments showed that in addition to the chiral ligand, conducting this transformation via Procedure C, which excludes the extensive prior coordination of the allene unit in the starting allene with Pd forming a species without the influence of the chiral ligand, is crucial for the observed high enantioselectivity.
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