ArticleOrganic letters2019
Kinetic Resolution of Cyclic Secondary Azides, Using an Enantioselective Copper-Catalyzed Azide-Alkyne Cycloaddition.
Article in Organic letters, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Novel, nanomagnetic and recoverable copper(0)-catalyst in one-pot access to 1,4-disubstituted 1,2,3-triazoles and 5-substituted 1Royal Society open science · 2025Article
- Enantioselective copper-catalyzed azidation/click cascade reaction for access to chiral 1,2,3-triazoles.Nature communications · 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
- Enantioselective Nickel-Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution.Journal of the American Chemical Society · 2021Article
- Article
- Divergent Mechanisms of the Banert Cascade with Propargyl Azides.The Journal of organic chemistry · 2020Article
- Enantioselective synthesis ofChemical science · 2020Article
- Coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation.Scientific reports · 2019Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
An enantioselective copper-catalyzed azide-alkyne cycloaddition (E-CuAAC) is reported by kinetic resolution. Chiral triazoles were isolated in high yield with limiting alkyne (up to 97:3 enantiomeric ratio (er)). A range of substrates were tolerated (>30 examples), and the reaction was scaled to >1 g. The er of a triazole product could be enhanced by recrystallization and the recovered scalemic azide could be racemized and recycled. Recycling the azide allows efficient use of the undesired azide enantiomer.
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