Taming Radical Intermediates for the Construction of Enantioenriched Trifluoromethylated Quaternary Carbon Centers |
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Authors: | Roxan Calvo Aleix Comas‐Vives Antonio Togni Dmitry Katayev |
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Abstract: | Demonstrated herein is the construction of trifluoromethylated quaternary carbon centers by an asymmetric radical transformation. Enantioenriched trifluoromethylated oxindoles were accessed using a hypervalent iodine‐based trifluoromethyl transfer reagent in combination with a magnesium Lewis acid catalyst and PyBOX‐type ligands to achieve up to 99 % ee and excellent chemical yields. Mechanistic studies were performed by experimental and computational methods and suggest a single‐electron transfer induced SN2‐type mechanism. This example is thereby the first report on the construction of enantioenriched trifluoromethylated carbon centers using hypervalent iodine‐based reagents proceeding through such a reaction pathway. |
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Keywords: | Asymmetrische Katalyse Heterocyclen Hypervalente Verbindungen Magnesium Radikale |
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