ArticleOrganic letters2014
Development of (trimethylsilyl)ethyl ester protected enolates and applications in palladium-catalyzed enantioselective allylic alkylation: intermolecular cross-coupling of functionalized electrophiles.
Article in Organic letters, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Bioinspired total synthesis of (+)-pleuromutilin.Nature communications · 2026Article
- Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications.Chemical reviews · 2021Article
- The Allylic Alkylation of Ketone Enolates.ChemistryOpen · 2020Review
- Direct Asymmetric Alkylation of Ketones: Still Unconquered.Angewandte Chemie (International ed. in English) · 2017Review
- Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations.Chemical reviews · 2017Article
- Iridium-Catalyzed Stereoselective Allylic Alkylation Reactions with Crotyl Chloride.Angewandte Chemie (International ed. in English) · 2016Article
- Concise Enantioselective Synthesis of Oxygenated Steroids via Sequential Copper(II)-Catalyzed Michael Addition/Intramolecular Aldol Cyclization Reactions.Journal of the American Chemical Society · 2015Article
- Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Cyclopentanones.Organic letters · 2015Article
- Cooperative benzylic-oxyallylic stabilized cations: regioselective construction of α-quaternary centers in ketone-derived compounds.Chemical science · 2015Article
- Synthesis and Exploration of Electronically Modified (Tetrahedron letters · 2015Article
- Catalytic enantioselective construction of quaternary stereocenters: assembly of key building blocks for the synthesis of biologically active molecules.Accounts of chemical research · 2015Article
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3 authors.
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Abstract
The development of (trimethylsilyl)ethyl ester protected enolates is reported. The application of this class of compounds in palladium-catalyzed asymmetric allylic alkylation is explored, yielding a variety of α-quaternary six- and seven-membered ketones and lactams. Independent coupling partner synthesis engenders enhanced allyl substrate scope relative to traditional β-ketoester substrates; highly functionalized α-quaternary ketones generated by the union of (trimethylsilyl)ethyl β-ketoesters and sensitive allylic alkylation coupling partners serve to demonstrate the utility of this method for complex fragment coupling.
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