ArticleiScience2020
Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles.
Article in iScience, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Asymmetric [3 + 2] Cycloaddition to Access 3-Pyrrolines and Their Switchable Transformations to Nine-Membered Cyclic Sulfamidates and 2H-Pyrroles.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Indole as a Versatile Building Block in Cycloaddition Reactions: Synthesis of Diverse Heterocyclic Frameworks.Topics in current chemistry (Cham) · 2024Review
- Catalytic asymmetric dearomatization of phenols via divergent intermolecular (3 + 2) and alkylation reactions.Nature communications · 2023Article
- Article
- Organocatalytic Asymmetric [2 + 4] Cycloadditions of 3-Vinylindoles withMolecules (Basel, Switzerland) · 2021Article
- Article
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Chiral phosphoric acid-catalyzed highly enantioselective formal [3 + 2] cycloaddition reaction of azoalkenes with 3-vinylindoles has been established. Under mild conditions, the projected cycloaddition proceeded smoothly, affording a variety of 2,3-dihydropyrroles in high yields and excellent enantioselectivities, and also in a diastereospecific manner. As opposed to the common 4-atom synthons in the previous literature reports, azoalkenes served as 3-atom synthons. Besides, the observed selectivity was supported by primary theoretical calculation. The unique chemistry of azoalkenes disclosed herein will empower asymmetric synthesis of nitrogen-containing ring structural motifs in a broader context.
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