ArticleOrganic letters2023
Photochemical Wolff Rearrangement Initiated Generation and Subsequent α-Chlorination of C1 Ammonium Enolates.
Article in Organic letters, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- From Oxygen to Tellurium: The Impact of the Chalcogen on Nucleophilicities and Basicities of Isochalcogenourea Catalysts.Angewandte Chemie (International ed. in English) · 2025Article
- α-Amination of 1,3-Dicarbonyl Compounds and Analogous Reactive Enolate-Precursors Using Ammonia under Oxidative Conditions.Angewandte Chemie (International ed. in English) · 2025Article
- Determination of the pEuropean journal of organic chemistry · 2025Article
- Enantioselective isothiourea-catalysed α-fluorination of C1-ammonium enolates generated from arylesters.Journal of fluorine chemistry · 2025Article
- Isochalcogenourea-catalyzed asymmetric (4 + 2)-heterocycloadditions of allenoates.Chemistry letters · 2024Article
- Enantioselective α-heterofunctionalization reactions of catalytically generated C1-Lewis base enolates.Tetrahedron chem · 2024Article
- Chiral Isochalcogenourea-Catalysed Enantioselective (4+2) Cycloadditions of Allenoates.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2024Article
- Chiral Isochalcogenourea-Catalysed Enantioselective (4+2) Cycloadditions of Allenoates.Angewandte Chemie (International ed. in English) · 2024Article
- Cooperative Chiral Lewis Base/Palladium-Catalyzed Asymmetric Syntheses of Methylene-Containing δ-Lactams.European journal of organic chemistry · 2023Article
- Chiral Lewis Base-Catalysed Asymmetric Syntheses of Benzo-fused ϵ-Lactones.European journal of organic chemistry · 2023Article
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Authors and funding
5 authors.
Funding
Abstract
The enantioselective synthesis of α-chlorinated carboxylic acid esters with er up to 99:1 and yields up to 82% was achieved via a one-pot multistep protocol starting from α-diazoketones. This process proceeds via a photochemical Wolff rearrangement, trapping of the generated ketene with a chiral Lewis base catalyst, subsequent enantioselective α-chlorination, and a final nucleophilic displacement of the bound catalyst. The obtained products were successfully utilized for stereospecific nucleophilic displacement reactions with
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