TY - JOUR
T1 - Asymmetric fluorination of β-keto esters catalyzed by chiral rare earth perfluorinated organophosphates
AU - Suzuki, Shoko
AU - Furuno, Hiroshi
AU - Yokoyama, Yasuo
AU - Inanaga, Junji
PY - 2006/2/20
Y1 - 2006/2/20
N2 - 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.
AB - 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.
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U2 - 10.1016/j.tetasy.2005.12.029
DO - 10.1016/j.tetasy.2005.12.029
M3 - Article
AN - SCOPUS:33645933298
VL - 17
SP - 504
EP - 507
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
SN - 0957-4166
IS - 4
ER -