ArticleJournal of the American Chemical Society2019
Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design.
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 24 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
24 citing papers in PubMed.
- Alcohol-Directed Carboamination of Conjugated Enynes.Angewandte Chemie (International ed. in English) · 2026Article
- Alkyne migratory functionalization via C(spNature communications · 2026Article
- Chemodivergent Coupling of 1,3-Enynes with Anilines to Access Dihydropyrrole Skeleton under Palladium Catalysis.Nature communications · 2026Article
- Multimodal Precise Control Over Multiselective Carbonylation of 1,3-Enynes.Journal of the American Chemical Society · 2025Article
- Tailored chiral phosphoramidites support highly enantioselective Pd catalysts for asymmetric aminoalkylative amination.Nature communications · 2024Article
- Escape from Hydrofunctionalization: Palladium Hydride-Enabled Difunctionalization of Conjugated Dienes and Enynes.Angewandte Chemie (International ed. in English) · 2023Article
- Nickel-catalysed asymmetric hydromonofluoromethylation of 1,3-enynes for enantioselective construction of monofluoromethyl-tethered chiral allenes.Chemical science · 2023Article
- Asymmetric formal spNature communications · 2023Article
- Synthesis of Allenes by Hydroalkylation of 1,3-Enynes with Ketones Enabled by Cooperative Catalysis.Journal of the American Chemical Society · 2023Article
- A Pd-catalyzed highly selective three-component protocol for trisubstituted allenes.Chemical science · 2023Article
- Progression of Hydroamination Catalyzed by Late Transition-Metal Complexes from Activated to Unactivated Alkenes.Accounts of chemical research · 2023Article
- Mechanism of Pd/Senphos-CatalyzedThe Journal of organic chemistry · 2023Article
- 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
- Direct access to spirocycles by Pd/WingPhos-catalyzed enantioselective cycloaddition of 1,3-enynes.Nature communications · 2021Article
- Chirality memory of α-methylene-π-allyl iridium species.Chemical science · 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
- Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications.Chemical reviews · 2021Article
- Late 3d Metal-Catalyzed (Cross-) Dimerization of Terminal and Internal Alkynes.Frontiers in chemistry · 2021Review
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
3 authors.
Funding
Abstract
In this study, we establish that conjugated enynes undergo selective 1,4-hydroamination under Pd catalysis to deliver chiral allenes with pendant allylic amines. Several primary and secondary aliphatic and aryl-substituted amines couple with a wide range of mono- and disubstituted enynes in a nonenantioselective reaction where DPEphos serves as the ligand for Pd. Benzophenone imine acts as an ammonia surrogate to afford primary amines in a two-step/one-pot process. Examination of chiral catalysts revealed a high degree of reversibility in the C-N bond formation that negatively impacted enantioselectivity. Consequently, an electron-poor ferrocenyl-PHOX ligand was developed to enable efficient and enantioselective enyne hydroamination.
Indexed as
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.