The organocatalytic enantiodivergent fluorination of β-ketodiaryl-phosphine oxides for the construction of carbon-fluorine quaternary stereocenters

Commercially available cinchona alkaloids that can catalyze the enantiodivergent fluorination of β-ketodiarylphosphine oxides were developed to construct carbon-fluorine quaternary stereocenters. This protocol features a wide scope of substrates and excellent enantioselectivities, and it is scalable...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2021-02, Vol.57 (16), p.269-272
Main Authors: Xie, Shaolei, He, Zhi-Juan, Zhang, Ling-Hui, Huang, Bo-Lun, Chen, Xiao-Wei, Zhan, Zong-Song, Zhang, Fu-Min
Format: Article
Language:English
Subjects:
Carbon
Crystallography
Fluorination
Fluorine
Phosphine oxide
Substrates
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Summary:Commercially available cinchona alkaloids that can catalyze the enantiodivergent fluorination of β-ketodiarylphosphine oxides were developed to construct carbon-fluorine quaternary stereocenters. This protocol features a wide scope of substrates and excellent enantioselectivities, and it is scalable. We developed, for the first time, the cinchona-alkaloid-catalyzed enantiodivergent α-fluorination of β-keto diarylphosphine oxides, which resulted in two enantiomers bearing fluorine-containing quaternary stereocenters.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc07770d