Taming Radical Intermediates for the Construction of Enantioenriched Trifluoromethylated Quaternary Carbon Centers
Metadata only
Datum
2019-01-28Typ
- Journal Article
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. Mehr anzeigen
Publikationsstatus
publishedExterne Links
Zeitschrift / Serie
Angewandte Chemie. International EditionBand
Seiten / Artikelnummer
Verlag
WileyThema
asymmetric catalysis; heterocycles; hypervalent compounds; magnesium; radicalsOrganisationseinheit
03872 - Copéret, Christophe / Copéret, Christophe
03363 - Togni, Antonio (emeritus) / Togni, Antonio (emeritus)
Förderung
168043 - Development of Novel Iron-Catalyzed Oxidative Transformations of Inert C(sp3)-H Bonds (SNF)