ArticleChemical science2023
Regiodivergent (3 + 2) annulation reactions of oxyallyl cations.
Article in Chemical science, 2023. 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.
- Diastereoselective synthesis of substituted cyclopentanonesChemical science · 2026Article
- Three-site cycloadditions within one reaction intermediate with site-selectivity controlled by electronic and size bias.Nature communications · 2026Article
- Asymmetric α-Alkylation With Activated and Unactivated Electrophiles by a Highly Productive and Recyclable Lewis Acid/Imidazolium Catalyst.Angewandte Chemie (International ed. in English) · 2026Article
- Synthesis of Indolyl-7-azanorbornanes by Decomposition of Tetrahydro-1,2,3-triazepines.Advanced synthesis & catalysis · 2025Article
- Selectivity Rules for the Dearomative (3+2) Annulation Reaction Between Substituted Indoles and Oxyallyl Cations.Advanced synthesis & catalysis · 2025Article
- Synthesis of Functionalized Hexahydrocarbazoles by Beckmann Elimination and Nucleophile-Intercepted Beckmann Fragmentation.Organic letters · 2024Article
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Authors and funding
4 authors.
Funding
Abstract
We report a new method for the regiodivergent dearomative (3 + 2) reaction between 3-substituted indoles and oxyallyl cations. Access to both regioisomeric products is possible and is contingent on the presence or absence of a bromine atom on the substituted oxyallyl cation. In this way, we are able to prepare molecules that contain highly-hindered, stereodefined, vicinal, quaternary centers. Detailed computational studies employing energy decomposition analysis (EDA) at the DFT level establishes that regiochemical control arises from either reactant distortion energy or orbital mixing and dispersive forces, depending on the oxyallyl cation. Examination of the Natural Orbitals for Chemical Valence (NOCV) confirms that indole acts as the nucleophilic partner in the annulation reaction.
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Registered trials
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