ArticleNature communications2022
Doubly stereoconvergent construction of vicinal all-carbon quaternary and tertiary stereocenters by Cu/Mg-catalyzed propargylic substitution.
Article in Nature communications, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Transient Boryl Assistance Enables Stereoselective Alkylation of Acyclic Tetrasubstituted Enolates.Angewandte Chemie (International ed. in English) · 2026Article
- Recent synthetic methodology advancements towards all-carbon quaternary center formation and applications.Tetrahedron · 2025Article
- Ni/Cu Dual-Catalyzed Propargylation for the Stereodivergent Synthesis of Methohexital.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Interplay of diruthenium catalyst in controlling enantioselective propargylic substitution reactions with visible light-generated alkyl radicals.Nature communications · 2023Article
- Enantioselective and Diastereodivergent Allylation of Propargylic C-H Bonds.Journal of the American Chemical Society · 2022Article
- Dealkenylative Alkynylation Using Catalytic FeJournal of the American Chemical Society · 2022Article
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Authors and funding
5 authors.
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Abstract
The construction of vicinal, congested stereocenters with high selectivities is of general utility in chemistry. To build two such stereocenters in one step from readily available starting materials is very desirable, but remains challenging. We report here a doubly stereoconvergent, Cu/Mg-catalyzed asymmetric propargylic substitution reaction to convert simple starting materials to products with vicinal tertiary and all-carbon quaternary stereocenters in high yields and excellent diastereo- and enantioselectivities. Both the nucleophiles and the electrophiles employed in this transformation are racemic. This reaction uses earth abundant metal catalysts, operates under ambient conditions, and demonstrates broad substrate scope. The products of this reaction are functional group rich and synthetically versatile. Key to the success of this development is the devise of a Cu/Mg dual catalytic system and the identification of a bulky tridentate pyridinebisimidazoline (PyBim) ligand.
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