ArticleNature communications2024
Accessing ladder-shape azetidine-fused indoline pentacycles through intermolecular regiodivergent aza-Paternò-Büchi reactions.
Article in Nature communications, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
What it found
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The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
4 citing papers in PubMed.
- Visible-Light-Mediated Lewis Acid-Catalyzed Diradical Hydrogen Atom Transfer Reaction of Enamides.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Triplet Energy Transfer-Driven Intermolecular [2+2] Photocycloaddition of Acyclic Imines and Indoles: Facile Access to Azetidine-Fused Indolines.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- A modular synthesis of azetidines from reactive triplet imine intermediates using an intermolecular aza Paternò-Büchi reaction.Nature catalysis · 2025Article
- Visible-Light-Induced Dearomative Annulation of Indoles toward Stereoselective Formation of Fused- and Spiro Indolines.ACS omega · 2024Review
Corrections and comments
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Authors and funding
10 authors.
Funding
Abstract
Small molecules with conformationally rigid, three-dimensional geometry are highly desirable in drug development, toward which a direct, simple-to-complexity synthetic logic is still of considerable challenges. Here, we report intermolecular aza-[2 + 2] photocycloaddition (the aza-Paternò-Büchi reaction) of indole that facilely assembles planar building blocks into ladder-shape azetidine-fused indoline pentacycles with contiguous quaternary carbons, divergent head-to-head/head-to-tail regioselectivity, and absolute exo stereoselectivity. These products exhibit marked three-dimensionality, many of which possess 3D score values distributed in the highest 0.5% region with reference to structures from DrugBank database. Mechanistic studies elucidated the origin of the observed regio- and stereoselectivities, which arise from distortion-controlled C-N coupling scenarios. This study expands the synthetic repertoire of energy transfer catalysis for accessing structurally intriguing architectures with high molecular complexity and underexplored topological chemical space.
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Registered trials
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