ArticleJournal of the American Chemical Society2022
Stereospecific Construction of Quaternary Carbon Stereocenters from Quaternary Carbon Stereocenters.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- Diastereoselective Synthesis of Axially Chiral Skipped Ene-Allenes Containing a Quaternary Stereocenter by Cyclopropene-Allene Metathesis.Angewandte Chemie (International ed. in English) · 2026Article
- The Role of 1,2-Palladium Migration/Insertion on C(spACS organic & inorganic Au · 2025Review
- Enantioselective intramolecular cyclopropanation via a cationic sulfoxonium-Rh-carbene.Nature communications · 2025Article
- Formally Stereoretentive SJournal of the American Chemical Society · 2025Article
- Stereospecific molecular rearrangement via nucleophilic substitution at quaternary stereocentres in acyclic systems.Nature chemistry · 2025Article
- Asymmetric Synthesis of Chiral 2-Cyclohexenones with Quaternary Stereocenters via Ene-Reductase Catalyzed Desymmetrization of 2,5-Cyclohexadienones.ACS catalysis · 2024Article
- Catalyst and Medium Control over Rebound Pathways in Manganese-Catalyzed Methylenic C-H Bond Oxidation.Journal of the American Chemical Society · 2024Article
- Nature-inspired catalytic asymmetric rearrangement of cyclopropylcarbinyl cation.Science advances · 2023Article
- Highly Diastereoselective Preparation of Tertiary Alkyl Isonitriles by Stereoinvertive Nucleophilic Substitution at a Nonclassical Carbocation.Organic letters · 2023Article
- Expedient synthesis of spiro[3.3]heptan-1-ones via strain-relocating semipinacol rearrangements.Tetrahedron · 2023Article
- Stereoselective Construction of Tertiary Homoallyl Alcohols and Ethers by Nucleophilic Substitution at Quaternary Carbon Stereocenters.Angewandte Chemie (International ed. in English) · 2023Article
- Synthesis and Functionalization of Tertiary Propargylic Boronic Esters by Alkynyllithium-Mediated 1,2-Metalate Rearrangement of Borylated Cyclopropanes.Organic letters · 2022Article
- Borylated Cyclopropanes as Spring-Loaded Entities: Access to Vicinal Tertiary and Quaternary Carbon Stereocenters in Acyclic Systems.Journal of the American Chemical Society · 2022Article
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Authors and funding
3 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Organoaluminum species promote a smooth nucleophilic substitution at the quaternary carbon stereocenter of stereodefined polysubstituted cyclopropyl methyl phosphate with a complete inversion of configuration, even when more reactive functional groups are present. The regio- and diastereoselectivity of the substitution is attributed to the existence of a bicyclobutonium intermediate.
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Registered trials
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