Asymmetric construction of allylicstereogenic carbon center featuring atrifluoromethyl group via enantioselective reductive fluoroalkylation

Ruo-Xing Jin, Bing-Bing Wu, Kang-Jie Bian, Jian-Liang Yu, Jing-Cheng Dai, Ya-Wen Zuo, Yi-Fan Zhang and Xi-Sheng Wang ()
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Ruo-Xing Jin: University of Science and Technology of China
Bing-Bing Wu: University of Science and Technology of China
Kang-Jie Bian: University of Science and Technology of China
Jian-Liang Yu: University of Science and Technology of China
Jing-Cheng Dai: University of Science and Technology of China
Ya-Wen Zuo: University of Science and Technology of China
Yi-Fan Zhang: University of Science and Technology of China
Xi-Sheng Wang: University of Science and Technology of China

Nature Communications, 2022, vol. 13, issue 1, 1-8

Abstract: Abstract 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 CF3 on aliphatic chain especially with the concomitant construction of trifluoromethylated alkanes bearing a CF3-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 CF3-containing chiral drugs and bioactive-molecules.

Date: 2022
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DOI: 10.1038/s41467-022-34841-1

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