ArticleFundamental research2023
Design and synthesis of axially chiral aryl-pyrroloindoles via the strategy of organocatalytic asymmetric (2 + 3) cyclization.
Article in Fundamental research, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Electrochemical cyclization of alkynes to construct five-membered nitrogen-heterocyclic rings.Beilstein journal of organic chemistry · 2025Review
- Recent advances in organocatalytic atroposelective reactions.Beilstein journal of organic chemistry · 2025Review
- Catalytic Asymmetric Diastereodivergent Synthesis of 2-Alkenylindoles Bearing both Axial and Central Chirality.Precision chemistry · 2024Article
- C(sp)-C(sp) Lever-Based Targets of Orientational Chirality: Design and Asymmetric Synthesis.Molecules (Basel, Switzerland) · 2024Article
- Organocatalytic diastereo- and atroposelective construction of N-N axially chiral pyrroles and indoles.Nature communications · 2024Article
- Organocatalytic intramolecular (4 + 2) annulation of enals with ynamides: atroposelective synthesis of axially chiral 7-aryl indolines.Chemical science · 2023Article
- Asymmetric Synthesis of Axially Chiral Molecules via Organocatalytic Cycloaddition and Cyclization Reactions.Molecules (Basel, Switzerland) · 2023Review
- Switchable synthesis of natural-product-like lawsones and indenopyrazoles through regioselective ring-expansion of indantrione.Communications chemistry · 2023Article
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8 authors.
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Abstract
The catalytic asymmetric construction of axially chiral indole-based frameworks is an important area of research due to the unique characteristics of such frameworks. Nevertheless, research in this area is still in its infancy and has some challenges, such as designing and constructing new classes of axially chiral indole-based scaffolds and developing their applications in chiral catalysts, ligands, etc. To overcome these challenges, we present herein the design and atroposelective synthesis of aryl-pyrroloindoles as a new class of axially chiral indole-based scaffolds via the strategy of organocatalytic asymmetric (2 + 3) cyclization between 3-arylindoles and propargylic alcohols. More importantly, this new class of axially chiral scaffolds was derived into phosphines, which served as efficient chiral ligands in palladium-catalyzed asymmetric reactions. Moreover, theoretical calculations provided an in-depth understanding of the reaction mechanism. This work offers a new strategy for constructing axially chiral indole-based scaffolds, which are promising for finding more applications in asymmetric catalysis.
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