N-trifluoromethylthiophthalimide: A stable electrophilic SCF 3-reagent and its application in the catalytic asymmetric trifluoromethylsulfenylation

Teerawut Bootwicha, Xiangqian Liu, Roman Pluta, Iuliana Atodiresei, Magnus Rueping*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

216 Scopus citations

Abstract

Cinchona alkaloid catalysts in combination with air- and moisture-stable N-trifluoromethylthiophthalimide as electrophilic SCF3 source enabled the catalytic enantioselective trifluoromethylsulfenylation. Thus, a series of α-SCF3 esters that bear a quaternary carbon stereogenic center were obtained with excellent yield and enantioselectivity. Moreover, the products can be readily converted into valuable α-SCF3 β-hydroxyesters.

Original languageEnglish (US)
Pages (from-to)12856-12859
Number of pages4
JournalAngewandte Chemie - International Edition
Volume52
Issue number49
DOIs
StatePublished - Dec 2 2013

Keywords

  • cinchona alkaloids
  • fluorine
  • indanones
  • organocatalysis
  • trifluoromethylsulfenylation

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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