ArticleAngewandte Chemie (International ed. in English)2016
Regiodivergent and Diastereoselective CuH-Catalyzed Allylation of Imines with Terminal Allenes.
Article in Angewandte Chemie (International ed. in English), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 37 papers.
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Who cites it
37 citing papers in PubMed.
- Copper-catalyzed enantioselective allylation of cyclic anhydrides for generation of multiple chiral centers.Nature communications · 2026Article
- Enantio- and Site-Selective Synthesis of α-Substituted Hydrazines, Pyrazolidines, and Tertiary Alcohols by Copper-Catalyzed Allylic C-N and C-O Bond Formation.Journal of the American Chemical Society · 2026Article
- Semi-Reduction of Allenes to Access Deuterated Allylic Isotopomers, Isotopologs and Enantioisotopomers.Angewandte Chemie (International ed. in English) · 2026Article
- 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
- Enantioconvergent Cobalt-Catalyzed Hydroalkylation for the Construction of Fluoro, Chloro, and Trifluoromethyl Stereogenic Centers.Angewandte Chemie (International ed. in English) · 2025Article
- 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
- 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
- A Diastereodivergent and Enantioselective Approach toJournal of the American Chemical Society · 2021Article
- Synthesis of 1,2-Aminoalcohols through Enantioselective Aminoallylation of Ketones by Cu-Catalyzed Reductive Coupling.Organic letters · 2021Article
- CuH-Catalyzed Regio- and Enantioselective Hydrocarboxylation of Allenes: Toward Carboxylic Acids with Acyclic Quaternary Centers.Journal of the American Chemical Society · 2021Article
- Access to Chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides.The Journal of organic chemistry · 2021Article
- Enantioselective C2-Allylation of Benzimidazoles Using 1,3-Diene Pronucleophiles.Organic letters · 2021Article
- Catalytic enantioselective allene-anhydride approach to β,γ-unsaturated enones bearing an α-all-carbon-quarternary center.Chemical science · 2020Article
- Evidence for Simultaneous Dearomatization of Two Aromatic Rings under Mild Conditions in Cu(I)-Catalyzed Direct Asymmetric Dearomatization of Pyridine.Journal of the American Chemical Society · 2020Article
- CuH-Catalyzed Olefin Functionalization: From Hydroamination to Carbonyl Addition.Accounts of chemical research · 2020Article
- Highly Enantioselective Synthesis of Indazoles with a C3-Quaternary Chiral Center Using CuH Catalysis.Journal of the American Chemical Society · 2020Article
- Enantio- and Diastereoselective Synthesis of Homopropargyl Amines by Copper-Catalyzed Coupling of Imines, 1,3-Enynes, and Diborons.Angewandte Chemie (International ed. in English) · 2020Article
- Diastereo- and Enantioselective Synthesis of Homoallylic Amines Bearing Quaternary Carbon Centers.Journal of the American Chemical Society · 2020Article
- Cu-catalyzed C-C bond formation of vinylidene cyclopropanes with carbon nucleophiles.Chemical science · 2019Article
- Access to a Catalytically Generated Umpolung Reagent through the Use of Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral Vicinal Aminoalcohol Synthons.Organic letters · 2019Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
A copper-catalyzed, chemoselective hydrometalation process enables the use of simple allenes as allylmetal nucleophile surrogates in imine allylation reactions. By modulating the nitrogen-protecting group, either highly branched- or linear-selective addition can be achieved from the same allene. Both reactions exhibit excellent diastereoselectivity and broad functional-group tolerance. Preliminary results indicate that good enantioselectivity can also be achieved in the linear-selective reaction. Finally, a mechanistic model for the regiodivergence is proposed on the basis of density functional theory calculations.
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