ArticleJournal of the American Chemical Society2018
A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with Terminal Allenes.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 40 papers.
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Who cites it
40 citing papers in PubMed.
- Copper-catalyzed enantioselective allylation of cyclic anhydrides for generation of multiple chiral centers.Nature communications · 2026Article
- Cobalt-Catalyzed Three-Component Reductive Coupling of Aldehydes, Allenes, and Aryl Halides.Organic letters · 2026Article
- Semi-Reduction of Allenes to Access Deuterated Allylic Isotopomers, Isotopologs and Enantioisotopomers.Angewandte Chemie (International ed. in English) · 2026Article
- Copper-Catalyzed Diastereo-, Enantio-, and (Journal of the American Chemical Society · 2024Article
- A catalytic process enables efficient and programmable access to precisely altered indole alkaloid scaffolds.Nature chemistry · 2024Article
- Copper Hydride-Catalyzed Enantioselective Olefin Hydromethylation.Journal of the American Chemical Society · 2022Article
- Boron-Catalyzed, Diastereo- and Enantioselective Allylation of Ketones with Allenes.ACS catalysis · 2022Article
- Chiral α-Stereogenic Oxetanols and AzetidinolsACS catalysis · 2022Article
- Confronting the Challenging Asymmetric Carbonyl 1,2-Addition Using Vinyl Heteroarene Pronucleophiles: Ligand-Controlled Regiodivergent Processes through a Dearomatized Allyl-Cu Species.Journal of the American Chemical Society · 2022Article
- Enantioselective Iridium-Catalyzed Reductive Coupling of Dienes with Oxetanones and N-Acyl-Azetidinones Mediated by 2-Propanol.Angewandte Chemie (International ed. in English) · 2022Article
- Allenes and Dienes as Chiral Allylmetal Pronucleophiles in Catalytic Enantioselective C=X Addition: Historical Perspective and State-of-The-Art Survey.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- Synthesis of 1,2-Aminoalcohols through Enantioselective Aminoallylation of Ketones by Cu-Catalyzed Reductive Coupling.Organic letters · 2021Article
- Access to enantioenriched compounds bearing challenging tetrasubstituted stereocenters via kinetic resolution of auxiliary adjacent alcohols.Nature communications · 2021Article
- Enantioselective Ruthenium-BINAP-Catalyzed Carbonyl Reductive Coupling of Alkoxyallenes: Convergent Construction ofJournal of the American Chemical Society · 2021Article
- CuH-Catalyzed Regio- and Enantioselective Hydrocarboxylation of Allenes: Toward Carboxylic Acids with Acyclic Quaternary Centers.Journal of the American Chemical Society · 2021Article
- Electroreductive Olefin-Ketone Coupling.Journal of the American Chemical Society · 2020Article
- 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(I)-catalyzed asymmetric 1,6-conjugate allylation.Nature communications · 2020Article
- 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
- Catalytic enantioselective allene-anhydride approach to β,γ-unsaturated enones bearing an α-all-carbon-quarternary center.Chemical science · 2020Article
Corrections and comments
- Erratum issued
Authors and funding
4 authors.
Funding
Abstract
We report a method for the highly enantioselective CuH-catalyzed allylation of ketones that employs terminal allenes as allylmetal surrogates. Ketones and allenes bearing diverse and sensitive functional groups are efficiently coupled with high stereoselectivity and exclusive branched regioselectivity. In stoichiometric experiments, each elementary step of the proposed hydrocupration-addition-metathesis mechanism can be followed by NMR spectroscopy.
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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.