ArticleAngewandte Chemie (International ed. in English)2019
Catalytic Enantioselective Ynamide Additions to Isatins: Concise Access to Oxindole Alkaloids.
Article in Angewandte Chemie (International ed. in English), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Asymmetric formal [1 + 2 + 2]-cycloaddition of diazoamides with enamines and carbonyl compounds.Nature communications · 2025Article
- One-Pot Access to Functionalised Malamides via Organocatalytic Enantioselective Formation of Spirocyclic β-Lactone-Oxindoles and Double Ring-Opening.Molecules (Basel, Switzerland) · 2024Article
- Ir/Zn-cocatalyzed chemo- and atroposelective [2+2+2] cycloaddition for construction of C─N axially chiral indoles and pyrroles.Science advances · 2023Article
- Asymmetric synthesis with ynamides: unique reaction control, chemical diversity and applications.Chemical Society reviews · 2020Article
- Catalytic Asymmetric Allylic Amination with Isatins, Sulfonamides, Imides, Amines, andOrganic letters · 2020Article
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Authors and funding
2 authors.
Funding
Abstract
The highly enantioselective addition of terminal ynamides to a variety of isatins, catalyzed by a bisoxazolidine copper complex under mild, base-free reaction conditions, is described. The reaction is broad in scope, scalable, applicable to unprotected isatins, and provides efficient access to 3-hydroxyoxindoles carrying a tetrasubstituted chiral center with excellent yields and enantioselectivities. Synthetically versatile, multifunctional 3-hydroxyindolinones are obtained by hydration, partial hydrogenation, or hydroxyacyloxylation of the ynamide moiety at room temperature and exhaustive hydrogenation followed by reductive detosylation and spontaneous cyclization affords cinchonamidine alkaloids.
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