ArticleChemical science2020
Catalytic enantioselective allene-anhydride approach to β,γ-unsaturated enones bearing an α-all-carbon-quarternary center.
Article in Chemical science, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Copper-catalyzed enantioselective allylation of cyclic anhydrides for generation of multiple chiral centers.Nature communications · 2026Article
- Diversity-Oriented Method Development: Multifunctional Homoallylic Amines and Azabicyclooctanes Bearing a Bridgehead Enamine.Journal of the American Chemical Society · 2025Article
- Light-Driven Enantioselective Carbene-Catalyzed Radical-Radical Coupling.Angewandte Chemie (International ed. in English) · 2023Article
- Direct allylic acylation via cross-coupling involving cooperative N‑heterocyclic carbene, hydrogen atom transfer, and photoredox catalysis.Nature communications · 2023Article
- A Catalytic Method for the Enantioselective Synthesis of α-Quaternary Ketones, α-Ketoesters and Aldehydes.Angewandte Chemie (International ed. in English) · 2023Article
- Copper-catalyzed regio- and stereo-selective hydrosilylation of terminal allenes to access (E)-allylsilanes.Nature communications · 2022Article
- Late-Stage Diversification: A Motivating Force in Organic Synthesis.Journal of the American Chemical Society · 2021Article
- Iron-Catalyzed Contrasteric Functionalization of Allenic C(spJournal of the American Chemical Society · 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
- CuH-Catalyzed Regio- and Enantioselective Hydrocarboxylation of Allenes: Toward Carboxylic Acids with Acyclic Quaternary Centers.Journal of the American Chemical Society · 2021Article
- 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
4 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
A protocol of highly regio- and enantioselective copper-catalyzed hydroacylation of the non-terminal C[double bond, length as m-dash]C bond in 1,1-disubstituted terminal allenes with anhydrides has been developed. Both aromatic and aliphatic carboxylic anhydrides are applicable to the efficient construction of all carbon quarternary centers connected with a versatile C[double bond, length as m-dash]C bond and a useful ketone functionality. The synthetic potentials of the enantioenriched products have also been demonstrated. Density functional theory (DFT) calculations were performed to explain the steric outcome of the products: the hydroacylation proceeds through a six-membered transition state and the ligand-substrate steric interactions account for the observed enantioselectivity although the chiral ligand is far away from the to-be-genetated chiral center.
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Registered trials
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