Taming Radical Intermediates for the Construction of Enantioenriched Trifluoromethylated Quaternary Carbon Centers

Roxan Calvo, Aleix Comas-Vives, Antonio Togni, Dmitry Katayev

Research output: Contribution to journalArticleResearch

19 Citations (Scopus)

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 languageEnglish
Pages (from-to)1447-1452
JournalAngewandte Chemie - International Edition
Volume58
DOIs
Publication statusPublished - 28 Jan 2019

Keywords

  • asymmetric catalysis
  • heterocycles
  • hypervalent compounds
  • magnesium
  • radicals

Fingerprint

Dive into the research topics of 'Taming Radical Intermediates for the Construction of Enantioenriched Trifluoromethylated Quaternary Carbon Centers'. Together they form a unique fingerprint.

Cite this