ArticleScience (New York, N.Y.)2019
Delayed catalyst function enables direct enantioselective conversion of nitriles to NH
Article in Science (New York, N.Y.), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
What it found
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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.
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Who cites it
23 citing papers in PubMed, 109 citations in OpenAlex.
- Enantioselective Synthesis of a New Class of Stable and Functionalized Cyclopentadienes via CuH-Catalysis.Angewandte Chemie (International ed. in English) · 2026Article
- Diversity-Oriented Method Development: Multifunctional Homoallylic Amines and Azabicyclooctanes Bearing a Bridgehead Enamine.Journal of the American Chemical Society · 2025Article
- Nickel-Catalyzed Cyanation of Aryl Halides.Molecules (Basel, Switzerland) · 2025Review
- Nickel-catalyzed domino annulation coupling to construct oxindole analogues: A mechanistic and synthetic investigation.iScience · 2025Article
- Synthesis of Chiral δ-Aminoboronic Esters by Enantioselective Hydrogenation of 1,2-Azaborines.Angewandte Chemie (International ed. in English) · 2025Article
- Evolving ω-amine transaminaseApplied and environmental microbiology · 2024Article
- Click processes orthogonal to CuAAC and SuFEx forge selectively modifiable fluorescent linkers.Nature chemistry · 2024Article
- Nitrenium ions as new versatile reagents for electrophilic amination.Chemical science · 2023Article
- Asymmetric Syntheses of (Journal of the American Chemical Society · 2023Article
- Copper-catalyzed defluorinative arylboration of vinylarenes with polyfluoroarenes.Chemical science · 2023Article
- Multicatalysis protocol enables direct and versatile enantioselective reductive transformations of secondary amides.Science advances · 2022Article
- An enantioselective four-component reaction via assembling two reaction intermediates.Nature communications · 2022Article
- Catalytic Lewis Base Additive Enables Selective Copper-Catalyzed Borylative α-C-H Allylation of Alicyclic Amines.Journal of the American Chemical Society · 2022Article
- DFT-Based Stereochemical Rationales for the Bifunctional Brønsted Acid/Base-Catalyzed Diastereodivergent and Enantioselective aza-Henry Reactions of α-Nitro Esters.The Journal of organic chemistry · 2021Article
- Synthesis of 1,2-Aminoalcohols through Enantioselective Aminoallylation of Ketones by Cu-Catalyzed Reductive Coupling.Organic letters · 2021Article
- Access to Chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides.The Journal of organic chemistry · 2021Article
- Reductive Arylation of Amides via a Nickel-Catalyzed Suzuki-Miyaura-Coupling and Transfer-Hydrogenation Cascade.Angewandte Chemie (International ed. in English) · 2021Article
- Sulfonate N-Heterocyclic Carbene-Copper Complexes: Uniquely Effective Catalysts for Enantioselective Synthesis of C-C, C-B, C-H, and C-Si Bonds.Angewandte Chemie (International ed. in English) · 2020Review
- Copper-Catalyzed Borylative Couplings with C-N Electrophiles.Angewandte Chemie (International ed. in English) · 2020Review
- Streamlined Catalytic Enantioselective Synthesis of α-Substituted β,γ-Unsaturated Ketones and Either of the Corresponding Tertiary Homoallylic Alcohol Diastereomers.Journal of the American Chemical Society · 2020Article
Corrections and comments
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Authors and funding
6 authors at 1 institution in 2 countries.
Funding
Abstract
Accessing enantiomerically enriched amines often demands oxidation-state adjustments, protection and deprotection processes, and purification procedures that increase cost and waste, limiting applicability. When diastereomers can be formed, one isomer is attainable. Here, we show that nitriles, largely viewed as insufficiently reactive, can be transformed directly to multifunctional unprotected homoallylic amines by enantioselective addition of a carbon-based nucleophile and diastereodivergent reduction of the resulting ketimine. Successful implementation requires that competing copper-based catalysts be present simultaneously and that the slower-forming and less reactive one engages first. This challenge was addressed by incorporation of a nonproductive side cycle, fueled selectively by inexpensive additives, to delay the function of the more active catalyst. The utility of this approach is highlighted by its application to the efficient preparation of the anticancer agent (+)-tangutorine.
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.