ArticleNature communications2019
Synergetic iridium and amine catalysis enables asymmetric [4+2] cycloadditions of vinyl aminoalcohols with carbonyls.
Article in Nature communications, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
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- Dynamic radical recombination enabling stereodivergent construction of spirocycles with nonadjacent stereocenters.Nature communications · 2025Article
- Enantiopure Turbo Chirality Targets in Tri-Propeller Blades: Design, Asymmetric Synthesis, and Computational Analysis.Molecules (Basel, Switzerland) · 2025Article
- Ni/Cu Dual-Catalyzed Propargylation for the Stereodivergent Synthesis of Methohexital.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Copper/ruthenium relay catalysis enables 1,6-double chiral inductions with stereodivergence.Chemical science · 2024Article
- 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
- Enantio- and diastereodivergent synthesis of fused indolizines enabled by synergistic Cu/Ir catalysis.Chemical science · 2023Article
- Catalytic Asymmetric α-Functionalization of α-Branched Aldehydes.Molecules (Basel, Switzerland) · 2023Review
- Development of Immobilized Carreira (Phosphoramidite, Olefin) Ligands and Application in Iridium-Catalyzed Asymmetric Allylic Amination.The Journal of organic chemistry · 2023Article
- Ligand-dependent, palladium-catalyzed stereodivergent synthesis of chiral tetrahydroquinolines.Chemical science · 2022Article
- Water enables diastereodivergency in bispidine-based chiral amine-catalyzed asymmetric Mannich reaction of cyclicChemical science · 2022Article
- Stereodivergent propargylic alkylation of enals via cooperative NHC and copper catalysis.Nature communications · 2022Article
- Borane-catalyzed cascade Friedel-Crafts alkylation/[1,5]-hydride transfer/Mannich cyclization to afford tetrahydroquinolines.Chemical science · 2022Article
- Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications.Chemical reviews · 2021Article
- H-bond donor-directed switching of diastereoselectivity in the Michael addition of α-azido ketones to nitroolefins.Chemical science · 2020Article
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6 authors.
Funding
Abstract
Catalytic asymmetric cycloadditions via transition-metal-containing dipolar intermediates are a powerful tool for synthesizing chiral heterocycles. However, within the field of palladium catalysis, compared with the well-developed normal electron-demand cycloadditions with electrophilic dipolarophiles, a general strategy for inverse electron-demand ones with nucleophilic dipolarophiles remains elusive, due to the inherent linear selectivity in the key palladium-catalyzed intermolecular allylations. Herein, based on the switched regioselectivity of iridium-catalyzed allylations, we achieved two asymmetric [4+2] cycloadditions of vinyl aminoalcohols with aldehydes and β,γ-unsaturated ketones through synergetic iridium and amine catalysis. The activation of vinyl aminoalcohols by iridium catalysts and carbonyls by amine catalysts provide a foundation for the subsequent asymmetric [4+2] cycloadditions of the resulting iridium-containing 1,4-dipoles and (di)enamine dipolarophiles. The former provides a straightforward route to a diverse set of enantio-enriched hydroquinolines bearing chiral quaternary stereocenters, and the later represent an enantio- and diastereodivergent synthesis of chiral hydroquinolines.
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