ArticleJournal of the American Chemical Society2019
CuH-Catalyzed Enantioselective Ketone Allylation with 1,3-Dienes: Scope, Mechanism, and Applications.
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 40 papers.
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Who cites it
40 citing papers in PubMed, 197 citations in OpenAlex.
- Recognition of a Conserved Minimal Catalaphile Explains Catalyst Generality in Enantioselective Nitroalkene Reductions.ACS catalysis · 2026Article
- Asymmetric Ketone Diene Coupling via Stereodivergent Copper Catalysis.Journal of the American Chemical Society · 2026Article
- Enantioselective Syntheses of Secondary Alkylboronates via Asymmetric Regioselective Reduction of 1,3-Dienylboronates.Angewandte Chemie (International ed. in English) · 2026Article
- Kinetics and Mechanism of Enantioselective Cu-Catalyzed Alcohol Silylation.Journal of the American Chemical Society · 2025Article
- Preparation of 1,4-Diamines by Enantio- and Diastereoselective Cu-Josiphos-Catalyzed Reductive Couplings of Azatrienes and Imines: Regiodivergence Enabled by Catalyst Structure and Reagent Tailoring.Journal of the American Chemical Society · 2025Article
- 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
- CuH-Catalyzed Regio- and Enantioselective Formal Hydroformylation of Vinyl Arenes.Journal of the American Chemical Society · 2024Article
- Copper-Catalyzed Asymmetric Acylboration of 1,3-Butadienylboronate with Acyl Fluorides.Angewandte Chemie (International ed. in English) · 2023Article
- Asymmetric Syntheses of (Journal of the American Chemical Society · 2023Article
- Stereoselective Construction of Tertiary Homoallyl Alcohols and Ethers by Nucleophilic Substitution at Quaternary Carbon Stereocenters.Angewandte Chemie (International ed. in English) · 2023Article
- Nickel-Catalyzed Enantioselective Coupling of Aldehydes and Electron-Deficient 1,3-Dienes Following an Inverse Regiochemical Course.Journal of the American Chemical Society · 2022Article
- 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
- A Dual CuH- and Pd-Catalyzed Stereoselective Synthesis of Highly Substituted 1,3-Dienes.Organic letters · 2021Article
- 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
- Generation of Axially Chiral Fluoroallenes through a Copper-Catalyzed Enantioselective β-Fluoride Elimination.Journal of the American Chemical Society · 2021Article
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Authors and funding
6 authors at 2 institutions in 1 country.
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Abstract
Chiral tertiary alcohols are important building blocks for the synthesis of pharmaceutical agents and biologically active natural products. The addition of carbon nucleophiles to ketones is the most common approach to tertiary alcohol synthesis but traditionally relies on stoichiometric organometallic reagents that are difficult to prepare, sensitive, and uneconomical. We describe a mild and efficient method for the copper-catalyzed allylation of ketones using widely available 1,3-dienes as allylmetal surrogates. Homoallylic alcohols bearing a wide range of functional groups are obtained in high yield and with good regio-, diastereo-, and enantioselectivity. Mechanistic investigations using density functional theory (DFT) implicate the in situ formation of a rapidly equilibrating mixture of isomeric copper(I) allyl complexes, from which Curtin-Hammett kinetics determine the major isomer of the product. A stereochemical model is provided to explain the high diastereo- and enantioselectivity of this process. Finally, this method was applied to the preparation of an important drug, ( R)-procyclidine, and a key intermediate in the synthesis of several pharmaceuticals.
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