ArticleNature communications2022
Stereodivergent propargylic alkylation of enals via cooperative NHC and copper catalysis.
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 13 papers.
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13 citing papers in PubMed, 76 citations in OpenAlex.
- Review
- Stereodivergent Access to Aliphatic Nitro Compounds Bearing Multi-Contiguous Stereocenters via Sequential Catalysis.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Dynamic radical recombination enabling stereodivergent construction of spirocycles with nonadjacent stereocenters.Nature communications · 2025Article
- Future Trends in Asymmetric Organo-Metal Combined Catalysis.ACS central science · 2025Review
- Catalytic Asymmetric Diastereodivergent Synthesis of 2-Alkenylindoles Bearing both Axial and Central Chirality.Precision chemistry · 2024Article
- Stereodivergent synthesis of α-fluoro α-azaaryl γ-butyrolactonesFundamental research · 2024Article
- Catalytic stereodivergent allylic alkylation of 2-acylimidazoles for natural product synthesis.Nature communications · 2023Article
- Enantioselective SAdvanced science (Weinheim, Baden-Wurttemberg, Germany) · 2023Article
- Silver/chiral pyrrolidinopyridine relay catalytic cycloisomerization/(2 + 3) cycloadditions of enynamides to asymmetrically synthesize bispirocyclopentenes as PDE1B inhibitors.Communications chemistry · 2023Article
- Asymmetric redox benzylation of enals enabled by NHC/Ru cooperative catalysis.Science advances · 2023Article
- Enantio- and diastereodivergent synthesis of fused indolizines enabled by synergistic Cu/Ir catalysis.Chemical science · 2023Article
- Reactions of noble-metal oxides in ionic liquids near room temperature.RSC advances · 2023Article
- Interplay of diruthenium catalyst in controlling enantioselective propargylic substitution reactions with visible light-generated alkyl radicals.Nature communications · 2023Article
Corrections and comments
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Despite that asymmetric stereodivergent synthesis has experienced great success to provide unusual processes for the creation of chirality complexity, concepts appliable to asymmetric stereodivergent catalysis are still limited. The dependence on the unusual capacity of each catalyst to precisely control the reactive site planar in the region poses unparalleled constraints on this field. Here, we first demonstrate that the chiral Cu-allenylidene species can participate in the stereodivergent propargylic alkylation of enals, in concert with chiral N-heterocyclic carbenes (NHCs). Thus, all four stereoisomers were obtained with excellent enantioselectivity and diastereoselectivity (up to >99% e.e. and >95:5 d.r.) from the same starting materials by simply altering chiral Cu-Pybox complex and NHC combinations. The rich chemistry workable in the products enables the structurally diverse synthesis of chiral functional molecules and holds great potential in alkaloid synthesis, as showcased by the preparation of the key building block to access (-)-perophoramidine.
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