ArticleACS catalysis2019
Catalytic Asymmetric Mannich Reaction of α-Fluoronitriles with Ketimines: Enantioselective and Diastereodivergent Construction of Vicinal Tetrasubstituted Stereocenters.
Article in ACS catalysis, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed.
- Enantioselective Construction of Fluorinated Tertiary Stereocenters by Rh-Catalyzed [2 + 2 + 2] Cycloaddition of 1,6-Enynes with α-Fluoroacrylamides.Organic letters · 2025Article
- Accessing acyclic vicinal tetrasubstituted stereocenters via biomimetic Cu/squaramide cooperative catalysed asymmetric Mannich reactions.Nature communications · 2025Article
- Asymmetric synthesis of β-amino cyanoesters with contiguous tetrasubstituted carbon centers by halogen-bonding catalysis with chiral halonium salt.Beilstein journal of organic chemistry · 2025Article
- Optical Enantiodifferentiation of Chiral Nitriles.Organic letters · 2024Article
- Recent Progress in Synthesis of Alkyl Fluorinated Compounds with Multiple Contiguous Stereogenic Centers.Molecules (Basel, Switzerland) · 2024Review
- Organocatalytic Asymmetric Conjugate Addition of Fluorooxindoles to Quinone Methides.The Journal of organic chemistry · 2024Article
- Challenges and recent advancements in the synthesis of α,α-disubstituted α-amino acids.Nature communications · 2024Review
- Enantioseparation and racemization of 3-fluorooxindoles.Chirality · 2023Article
- Selective CspSynthesis · 2022Article
- Catalytic Asymmetric Allylic Alkylation with Arylfluoroacetonitriles.The Journal of organic chemistry · 2022Article
- Chemodivergent CspScience advances · 2022Article
- Catalytic stereoselective Mannich-type reactions for construction of fluorinated compounds.Molecular diversity · 2022Review
- Fluorine-induced diastereodivergence discovered in an equally rare enantioselectiveChemical science · 2022Article
- Article
- Palladium and Nickel Catalyzed Suzuki Cross-Coupling with Alkyl Fluorides.Organic letters · 2021Article
- Switchable, Reagent-Controlled Diastereodivergent Photocatalytic Carbocyclisation of Imine-Derived α-Amino Radicals.Angewandte Chemie (International ed. in English) · 2021Article
- Asymmetric Catalytic Ketimine Mannich Reactions and Related Transformations.Catalysts (Basel, Switzerland) · 2021Article
- Construction of chiral α-Chemical science · 2020Article
- Catalytic Asymmetric Allylic Amination with Isatins, Sulfonamides, Imides, Amines, andOrganic letters · 2020Article
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3 authors.
Funding
Abstract
Diastereodivergent and enantioselective conversion of isatin ketimines to α-fluoro-β-aminonitriles with vicinal tetrasubstituted stereocenters is achieved by a chiral copper complex/guanidine base catalyzed Mannich reaction with proper choice of the bisphosphine ligand. The reaction is broad in scope, scalable, and provides efficient access to a series of 3-aminoindolinones exhibiting a quaternary carbon-fluorine stereocenter with high yields and stereoselectivities. Selective transformations of the Mannich reaction products into multifunctional 3-aminooxindoles without erosion of enantiomeric and diastereomeric purity highlight the synthetic utility.
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