Asymmetric fluorination of β-keto esters catalyzed by chiral rare earth perfluorinated organophosphates

Shoko Suzuki, Hiroshi Furuno, Yasuo Yokoyama, Junji Inanaga

Research output: Contribution to journalArticle

70 Citations (Scopus)

Abstract

Novel chiral rare earth metal complexes bearing perfluorinated binaphthyl phosphate ligand RE[(R)-F8BNP]3 (RE = rare earth; F8BNP = 5,5′,6,6′,7,7′,8,8′-octafluoro-1,1′-binaph thyl-2,2′-diyl phosphate) have been synthesized and used as a catalyst for the asymmetric electrophilic fluorination reaction of β-keto esters. The use of Sc[(R)-F8BNP]3 catalyst in combination with 1-fluoropyridinium triflate (NFPY-OTf) as a fluorinating agent was found to give the desired α-fluoro-β-keto esters in high chemical yields and enantiomeric excesses (up to 88% ee) under mild conditions.

Original languageEnglish
Pages (from-to)504-507
Number of pages4
JournalTetrahedron Asymmetry
Volume17
Issue number4
DOIs
Publication statusPublished - Feb 20 2006

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Fluorination
fluorination
Organophosphates
Rare earths
esters
Esters
phosphates
Phosphates
Rare Earth Metals
Bearings (structural)
rare earth elements
catalysts
Catalysts
Coordination Complexes
Metal complexes
Ligands
ligands
metals

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Asymmetric fluorination of β-keto esters catalyzed by chiral rare earth perfluorinated organophosphates. / Suzuki, Shoko; Furuno, Hiroshi; Yokoyama, Yasuo; Inanaga, Junji.

In: Tetrahedron Asymmetry, Vol. 17, No. 4, 20.02.2006, p. 504-507.

Research output: Contribution to journalArticle

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