ArticleNature chemistry2021
Catalytic reductive desymmetrization of malonic esters.
Article in Nature chemistry, 2021. 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.
- Dyotropic Rearrangement of Hypervalent Iodine Species: Migrative Heterofunctionalization of Quaternary Carbons.Angewandte Chemie (International ed. in English) · 2026Article
- A unified and desymmetric approach to axially chiral atropisomers.Nature communications · 2026Article
- Desymmetrization of Malonic Monoesters and Malonic Acids via Enantioselective Catalytic C(spAngewandte Chemie (International ed. in English) · 2026Article
- Artificial Chiral Trinuclear Zn Catalysts: Design, Self-Assembly and Unprecedented Efficiency in Asymmetric Hydroboration of Ketones.ACS central science · 2025Article
- The application of desymmetric enantioselective reduction of cyclic 1,3-dicarbonyl compounds in the total synthesis of terpenoid and alkaloid natural products.Beilstein journal of organic chemistry · 2025Review
- Cobalt-catalysed desymmetrization of malononitriles via enantioselective borohydride reduction.Nature chemistry · 2024Article
- Palladium-catalyzed asymmetric hydrogenation of lactones under base-free conditions.Chemical science · 2024Article
- Nickel-catalysed asymmetric hydromonofluoromethylation of 1,3-enynes for enantioselective construction of monofluoromethyl-tethered chiral allenes.Chemical science · 2023Article
- Amino Acid-Derived Ionic Chiral Catalysts Enable Desymmetrizing Cross-Coupling to Remote Acyclic Quaternary Stereocenters.Journal of the American Chemical Society · 2023Article
- Nickel-catalyzed regio- and enantio-selective Markovnikov hydromonofluoroalkylation of 1,3-dienes.Chemical science · 2022Article
- Diverse synthesis of α-tertiary amines and tertiary alcohols via desymmetric reduction of malonic esters.Nature communications · 2022Article
- Distal Ionic Substrate-Catalyst Interactions Enable Long-Range Stereocontrol: Access to Remote Quaternary Stereocenters through a Desymmetrizing Suzuki-Miyaura Reaction.Journal of the American Chemical Society · 2022Article
- The gains from breaking symmetry.Nature chemistry · 2021Article
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2 authors.
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No grant is acknowledged in the PubMed record.
Abstract
Desymmetrization of fully substituted carbons with a pair of enantiotopic functional groups is a practical strategy for the synthesis of quaternary stereocentres, as it divides the tasks of enantioselection and C-C bond formation. The use of disubstituted malonic esters as the substrate of desymmetrization is particularly attractive, given their easy and modular preparation, as well as the high synthetic values of the chiral monoester products. Here, we report that a dinuclear zinc complex with a tetradentate ligand can selectively hydrosilylate one of the carbonyls of malonic esters to give α-quaternary β-hydroxyesters, providing a promising alternative to the desymmetric hydrolysis using carboxylesterases. The asymmetric reduction features excellent enantiocontrol that can differentiate sterically similar substituents and high chemoselectivity towards the diester motif of substrates. Together with the versatile preparation of malonic ester substrates and post-reduction derivatization, the desymmetric reduction has enabled the synthesis of a diverse array of quaternary stereocentres with distinct structural features.
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