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Asymmetric construction of allylicstereogenic carbon center featuring atrifluoromethyl group via enantioselective reductive fluoroalkylation
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Asymmetric construction of allylicstereogenic carbon center featuring atrifluoromethyl group via enantioselective reductive fluoroalkylation
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Asymmetric construction of allylicstereogenic carbon center featuring atrifluoromethyl group via enantioselective reductive fluoroalkylation
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Journal Article
Asymmetric construction of allylicstereogenic carbon center featuring atrifluoromethyl group via enantioselective reductive fluoroalkylation
2022
Overview
Emerging as a powerful tool for lead optimization in pharmaceutical research and development, to develop the facile, general protocols that allows the incorporation of fluorine-containing motif in drug candidates has accumulated enormous research interest in recent years. Among these important motifs, the incorporation of strategic motif CF
3
on aliphatic chain especially with the concomitant construction of trifluoromethylated alkanes bearing a CF
3
-substituted stereogenic carbon, is of paramount importance. Herein, we disclose an asymmetric nickel-catalyzed reductive trifluoroalkylation of alkenyl halides for enantioselective syntheses of diverse
α
-trifluoromethylated allylic alkanes, offering a general protocol to access the trifluoromethyl analogue to chiral
α
-methylated allylic alkanes, one of the most prevalent key components among natural products and pharmaceuticals. Utilities of the method including the application of the asymmetric trifluoroalkylation on multiple biologically active complex molecules, derivatization of transformable alkenyl functionality were demonstrated, providing a facile method in the diversity-oriented syntheses of CF
3
-containing chiral drugs and bioactive-molecules.
The efficient construction of trifluoromethylated alkanes bearing a CF
3
chiral center is of great importance in organic synthesis. Here, the authors disclose the enantioselective syntheses of α-trifluoromethylated allylic alkanes via reductive trifluoroalkylation.
