ArticleNature communications2019
Stereodivergent assembly of tetrahydro-γ-carbolines via synergistic catalytic asymmetric cascade reaction.
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 19 papers.
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Who cites it
19 citing papers in PubMed, 147 citations in OpenAlex.
- 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
- Stereodivergent synthesis of benzylic alcohol derivatives enabled by Pd/Cu co-catalyzed asymmetric benzylic substitution reaction.Nature communications · 2025Article
- The stereo-divergent functionalization of alkynes: a comprehensive review.RSC advances · 2025Review
- Stereodivergent assembly of δ-valerolactones with an azaarene-containing quaternary stereocenter enabled by Cu/Ru relay catalysis.Chemical science · 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
- Bimetallic Ru/Ru-Catalyzed Asymmetric One-Pot Sequential Hydrogenations for the Stereodivergent Synthesis of Chiral Lactones.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Catalytic Asymmetric Diastereodivergent Synthesis of 2-Alkenylindoles Bearing both Axial and Central Chirality.Precision chemistry · 2024Article
- Diastereo-divergent synthesis of chiral hindered ethers via a synergistic calcium(II)/gold(I) catalyzed cascade hydration/1,4-addition reaction.Nature communications · 2024Article
- Modular access to chiral bridged piperidine-γ-butyrolactones via catalytic asymmetric allylation/aza-Prins cyclization/lactonization sequences.Nature communications · 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
- EnantioconvergentOrganic letters · 2023Article
- Synergistic Li/Li Bimetallic System for the Asymmetric Synthesis of Antituberculosis Drug TBAJ-587.The Journal of organic chemistry · 2023Article
- Electron-rich benzofulvenes as effective dipolarophiles in copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides.Chemical science · 2023Article
- Enantio- and diastereodivergent synthesis of fused indolizines enabled by synergistic Cu/Ir catalysis.Chemical science · 2023Article
- Stereodivergent synthesis of enantioenriched azepino[3,4,5-Chemical science · 2022Article
- Stereodivergent propargylic alkylation of enals via cooperative NHC and copper catalysis.Nature communications · 2022Article
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Authors and funding
6 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Enantiomerically enriched indole-containing heterocycles play a vital role in bioscience, medicine, and chemistry. As one of the most attractive subtypes of indole alkaloids, highly substituted tetrahydro-γ-carbolines are the basic structural unit in many natural products and pharmaceuticals. However, the syntheses of tetrahydro-γ-carbolines with high functionalities from readily available reagents are significant challenging. In particular, the stereodivergent syntheses of tetrahydro-γ-carbolines containing multi-stereogenic centers remain quite difficult. Herein, we report an expedient and stereodivergent assembly of tetrahydro-γ-carbolines with remarkably high levels of stereoselective control in an efficient cascade process from aldimine esters and indolyl allylic carbonates via a synergistic Cu/Ir catalyst system. Control experiments-guided optimization of synergistic catalysts and mechanistic investigations reveal that a stereodivergent allylation reaction and a subsequent highly stereoselective iso-Pictet-Spengler cyclization are the key elements to success.
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