Decarboxylative Organocatalyzed Addition Reactions of Fluoroacetate Surrogates for the Synthesis of Fluorinated Oxindoles
Dominik Zetschok, Lukas Heieck, Helma Wennemers
Abstract
Fluorinated malonic acid half thioesters (F-MAHTs) were used as thioester enolate equivalents in organocatalyzed addition reactions to isatins. The products from a range of different N-protected and nonprotected isatins were obtained under mild reaction conditions in high yields and enantioselectivities. The unique reactivity of the thioester moiety enabled diverse derivatization and allowed for the straightforward access to a fluorinated analogue of the anticancer agent (S)-YK-4-279, a therapeutically active compound against Ewing’s sarcoma.
Topics & Concepts
ChemistryThioesterDerivatizationMoietyFluoroacetateElectrophileReactivity (psychology)Combinatorial chemistryOrganic chemistryBiochemistryCatalysisHigh-performance liquid chromatographyEnzymePathologyMedicineAlternative medicineFluorine in Organic ChemistryAsymmetric Synthesis and CatalysisSynthesis and Reactions of Organic Compounds