ArticleJournal of the American Chemical Society2021
Kinetic Resolution of Allyltriflamides through a Pd-Catalyzed C-H Functionalization with Allenes: Asymmetric Assembly of Tetrahydropyridines.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Total Synthesis of Isoriccardin C and Isoriccardin D Based on a Hydroxyl-Directed Palladium-Catalyzed Intramolecular C-H Alkenylation.Organic letters · 2026Article
- Substrate NOBINAc ligand affinity for PdChemical science · 2025Article
- Assembly of 2-Substituted Tetrahydroquinolines fromOrganic letters · 2024Article
- Axially Chiral 2-Hydroxybiaryls by Palladium-Catalyzed Enantioselective C-H Activation.ACS catalysis · 2023Article
- A palladium catalyzed asymmetric desymmetrization approach to enantioenriched 1,3-disubstituted isoindolines.Chemical science · 2023Article
- Chiral Ligands Based on Binaphthyl Scaffolds for Pd-Catalyzed Enantioselective C-H Activation/Cycloaddition Reactions.Journal of the American Chemical Society · 2022Article
- Mapping Ambiphile Reactivity Trends in the Anti-(Hetero)annulation of Non-Conjugated Alkenes via PdAngewandte Chemie (International ed. in English) · 2022Article
- Transition-Metal-Catalyzed Annulations Involving the Activation of C(spAngewandte Chemie (International ed. in English) · 2022Review
- Recent advances in palladium-catalyzed (hetero)annulation of C[double bond, length as m-dash]C bonds with ambiphilic organo(pseudo)halides.Chemical communications (Cambridge, England) · 2021Article
- On the application of 3d metals for C-H activation toward bioactive compounds: The key step for the synthesis of silver bullets.Beilstein journal of organic chemistry · 2021Review
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Authors and funding
4 authors.
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Abstract
Enantioenriched, six-membered azacycles are essential structural motifs in many products of pharmaceutical or agrochemical interest. Here we report a simple and practical method for enantioselective assembly of tetrahydropyridines, which is paired to a kinetic resolution of α-branched allyltriflamides. The reaction consists of a formal (4+2) cycloaddition between the allylamine derivatives and allenes and is initiated by a palladium(II)-catalyzed C-H activation process. Both the chiral allylamide precursors and the tetrahydropyridine adducts were successfully obtained in high yields, with excellent enantioselectivity (up to 99%
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