Abstract
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 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 S N 2-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.
Original language | English |
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Pages (from-to) | 1447-1452 |
Journal | Angewandte Chemie - International Edition |
Volume | 58 |
DOIs | |
Publication status | Published - 28 Jan 2019 |
Keywords
- asymmetric catalysis
- heterocycles
- hypervalent compounds
- magnesium
- radicals