ArticleNature communications2022
Organocatalytic cycloaddition of alkynylindoles with azonaphthalenes for atroposelective construction of indole-based biaryls.
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 9 papers.
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Who cites it
9 citing papers in PubMed.
- Regiodivergence in the Cycloadditions between a Cyclic Nitrone and Carbonyl-Type Dipolarophiles.The Journal of organic chemistry · 2025Article
- 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
- Pd-catalyzed asymmetric Larock reaction for the atroposelective synthesis of N─N chiral indoles.Science advances · 2024Article
- Dynamic Kinetic Resolution of Indole-Based Sulfenylated Heterobiaryls by Rhodium-Catalyzed Atroposelective Reductive Aldol Reaction.ACS catalysis · 2023Article
- Catalytic asymmetric indolization by a desymmetrizing [3 + 2] annulation strategy.Chemical science · 2023Article
- 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
- Advances in Atroposelectively De Novo Synthesis of Axially Chiral Heterobiaryl Scaffolds.Molecules (Basel, Switzerland) · 2022Review
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Authors and funding
9 authors.
Funding
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Abstract
The axially chiral indole-aryl motifs are present in natural products and biologically active compounds as well as in chiral ligands. Atroposelective indole formation is an efficient method to construct indole-based biaryls. We report herein the result of a chiral phosphoric acid catalyzed asymmetric cycloaddition of 3-alkynylindoles with azonaphthalenes. A class of indole-based biaryls were prepared efficiently with excellent yields and enantioselectivities (up to 98% yield, 99% ee). Control experiment and DFT calculations illustrate a possible mechanism in which the reaction proceeds via a dearomatization of indole to generate an allene-iminium intermediate, followed by an intramolecular aza-Michael addition. This approach provides a convergent synthetic strategy for enantioselective construction of axially chiral heterobiaryl backbones.
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