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

Shoko Suzuki; Hiroshi Furuno; Yasuo Yokoyama; Junji Inanaga

doi:10.1016/j.tetasy.2005.12.029

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

Shoko Suzuki, Hiroshi Furuno, Yasuo Yokoyama, Junji Inanaga

研究成果: Contribution to journal › Article › 査読

74 被引用数 (Scopus)

抄録

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.

本文言語	英語
ページ（範囲）	504-507
ページ数	4
ジャーナル	Tetrahedron Asymmetry
巻	17
号	4
DOI	https://doi.org/10.1016/j.tetasy.2005.12.029
出版ステータス	出版済み - 2 20 2006

All Science Journal Classification (ASJC) codes

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

文献へのアクセス

10.1016/j.tetasy.2005.12.029

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引用スタイル

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title = "Asymmetric fluorination of β-keto esters catalyzed by chiral rare earth perfluorinated organophosphates",

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.",

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AU - Suzuki, Shoko

AU - Furuno, Hiroshi

AU - Yokoyama, Yasuo

AU - Inanaga, Junji

PY - 2006/2/20

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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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