Lanthanum-Catalyzed Enantioselective Trifluoromethylation by Using an Electrophilic Hypervalent Iodine Reagent

Albert Granados, Iván Rivilla, Fernando P. Cossío, Adelina Vallribera

Research output: Contribution to journalArticleResearch

4 Citations (Scopus)

Abstract

© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim A highly enantioselective catalytic method for the synthesis of quaternary α-trifluoromethyl derivatives of 3-oxo esters is described. The reaction uses lanthanum(III) triflate and chiral PyBOX-type C2-symmetric ligands to generate intermediate LaIII complexes that incorporate an enolate moiety of the starting 3-oxo ester and the trifluoromethylation transfer reagent. The enantioselectivity of the reaction stems from the efficient blockage of one of the prochiral faces of the LaIII enolate by one unit of the C2-symmetric ligand.
Original languageEnglish
Pages (from-to)8214-8218
JournalChemistry - A European Journal
Volume25
DOIs
Publication statusPublished - 21 Jun 2019

Keywords

  • catalysis
  • density functional calculations
  • lanthanum
  • PyBOX
  • trifluoromethylation

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