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 language | English |
|---|---|
| Pages (from-to) | 504-507 |
| Number of pages | 4 |
| Journal | Tetrahedron Asymmetry |
| Volume | 17 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - Feb 20 2006 |
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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 journal › Article
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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.
UR - http://www.scopus.com/inward/record.url?scp=33645933298&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=33645933298&partnerID=8YFLogxK
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 -