ArticleAngewandte Chemie (International ed. in English)2017
Catalytic Enantioselective and Diastereoselective Allylic Alkylation with Fluoroenolates: Efficient Access to C3-Fluorinated and All-Carbon Quaternary Oxindoles.
Article in Angewandte Chemie (International ed. in English), 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 30 papers.
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Who cites it
30 citing papers in PubMed.
- Palladium-catalyzed asymmetric carbofluorination ofChemical communications (Cambridge, England) · 2026Article
- Cryogenic Organometallic Carbon-Fluoride Bond Functionalization with Broad Functional Group Tolerance.Journal of the American Chemical Society · 2025Article
- Recent Progress in Synthesis of Alkyl Fluorinated Compounds with Multiple Contiguous Stereogenic Centers.Molecules (Basel, Switzerland) · 2024Review
- Regioconvergent Nucleophilic Substitutions with Morita-Baylis-Hillman Fluorides.The Journal of organic chemistry · 2024Article
- Organocatalytic Asymmetric Conjugate Addition of Fluorooxindoles to Quinone Methides.The Journal of organic chemistry · 2024Article
- Enantioseparation and racemization of 3-fluorooxindoles.Chirality · 2023Article
- Organocuprate Cross-Coupling Reactions with Alkyl Fluorides.Organic letters · 2022Article
- Selective CspSynthesis · 2022Article
- Catalytic Asymmetric Allylic Alkylation with Arylfluoroacetonitriles.The Journal of organic chemistry · 2022Article
- Chemodivergent CspScience advances · 2022Article
- Catalytic alkene skeletal modification for the construction of fluorinated tertiary stereocenters.Chemical science · 2022Article
- Article
- Palladium and Nickel Catalyzed Suzuki Cross-Coupling with Alkyl Fluorides.Organic letters · 2021Article
- Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.Chemical reviews · 2021Article
- Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications.Chemical reviews · 2021Article
- 2-Fluoro-5-nitrophenyldiazonium: A Novel Sanger-Type Reagent for the Versatile Functionalization of Alcohols.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- A novel methodology for the efficient synthesis of 3-monohalooxindoles by acidolysis of 3-phosphate-substituted oxindoles with haloid acids.Beilstein journal of organic chemistry · 2021Article
- Catalytic Asymmetric Allylic Amination with Isatins, Sulfonamides, Imides, Amines, andOrganic letters · 2020Article
- Brønsted acid and Pd-PHOX dual-catalysed enantioselective addition of activated C-pronucleophiles to internal dienes.Chemical science · 2019Article
- Catalytic Enantioselective Ynamide Additions to Isatins: Concise Access to Oxindole Alkaloids.Angewandte Chemie (International ed. in English) · 2019Article
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2 authors.
Funding
Abstract
Synthetically versatile 3,3-disubstituted fluorooxindoles exhibiting vicinal chirality centers were obtained in high yields and with excellent enantio-, diastereo-, and regioselectivity through catalytic asymmetric fluoroenolate alkylation with allylic acetates. The reaction proceeds under mild conditions and can be scaled up without compromising the asymmetric induction. The unique synthetic usefulness of the products is highlighted by the incorporation of additional functionalities and the formation of 3-fluorinated oxindoles exhibiting an array of four adjacent centers of chirality. A new C-F bond functionalization path that provides unprecedented possibilities for the stereoselective generation of a chiral quaternary carbon center in the alkaloid scaffold is introduced.
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