ArticleJournal of the American Chemical Society2019
Enantioselective Copper Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution.
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 21 papers.
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Who cites it
21 citing papers in PubMed.
- Catalytic Enantioselective Construction of Planar Chiral Heterocyclic [2.2]Paracyclophanes Enabled by Copper-Catalyzed Desymmetric Azide-Alkyne Cycloaddition.Nature communications · 2026Article
- Copper-catalyzed enantioselective interrupted azide-alkyne cycloaddition to access axially chiral diaryl ethers.Chemical science · 2026Article
- Label-Free Target Discovery Strategy for Natural Active Products.Biomolecules · 2026Review
- Enantioselective copper-catalyzed azidation/click cascade reaction for access to chiral 1,2,3-triazoles.Nature communications · 2024Article
- Synthesis of chiral Cu(II) complexes from pro-chiral Schiff base ligand and investigation of their catalytic activity in the asymmetric synthesis of 1,2,3-triazoles.Scientific reports · 2024Article
- Copper-catalyzed atroposelective synthesis of C-O axially chiral compounds enabled by chiral 1,8-naphthyridine based ligands.Chemical science · 2024Article
- Enantioselective functionalization of unactivated C(spNature communications · 2024Article
- Germanyl triazoles as a platform for CuAAC diversification and chemoselective orthogonal cross-coupling.Beilstein journal of organic chemistry · 2024Article
- Asymmetric rhodium-catalyzed click cycloaddition to access C-N axially chiralChemical science · 2023Article
- Kinetic resolution of cyclic benzylic azides enabled by site- and enantioselective C(spNature communications · 2022Article
- Intercepting the Banert cascade with nucleophilic fluorine: direct access to α-fluorinatedChemical communications (Cambridge, England) · 2021Article
- Enantioselective Nickel-Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution.Journal of the American Chemical Society · 2021Article
- Water-Compatible Synthesis of 1,2,3-Triazoles under Ultrasonic Conditions by a Cu(I) Complex-Mediated Click Reaction.ACS omega · 2020Article
- A Cascade Reaction of Cinnamyl Azides with Acrylates Directly Generates Tetrahydro-Pyrrolo-Pyrazole Heterocycles.The Journal of organic chemistry · 2020Article
- Mechanical and Thermal Properties of Polyether Polytriazole Elastomers Formed by Click-Chemical Reaction Curing Glycidyl Azide Polymer.Molecules (Basel, Switzerland) · 2020Article
- Divergent Mechanisms of the Banert Cascade with Propargyl Azides.The Journal of organic chemistry · 2020Article
- Insight into the factors controlling the equilibrium of allylic azides.RSC advances · 2020Article
- Enantioselective synthesis ofChemical science · 2020Article
- Coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation.Scientific reports · 2019Article
- Kinetic Resolution of Cyclic Secondary Azides, Using an Enantioselective Copper-Catalyzed Azide-Alkyne Cycloaddition.Organic letters · 2019Article
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2 authors.
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Abstract
The copper(I) catalyzed alkyne-azide cycloaddition (CuAAC), a click reaction, is one of the most powerful catalytic reactions developed during the last two decades. Conducting CuAAC enantioselectively would add a third dimension to this reaction and would enable the direct synthesis of α-chiral triazoles. Doing so is demanding because the two precursors have linear geometries, and the triazole product is a flat heterocycle. Designing a chiral catalyst is further complicated by the complex mechanism of CuAAC. We report an enantioselective CuAAC (E-CuAAC), enabled by dynamic kinetic resolution (DKR). The E-CuAAC is high yielding and affords up to 99:1 er. The E-CuAAC can directly generate α-chiral triazoles in a complex molecular environment.
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