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Beilstein Arch. 2024, 202451. https://doi.org/10.3762/bxiv.2024.51.v1
Published 23 Jul 2024
Treatment of various (R)-N-(2,2,3,3-tetrafluoropent-4-en-1-ylidene)-1-phenylethylamine derivatives with 2.4 equiv. of DBU in toluene at room temperature to 50 °C for 24 h led to a smooth [1,3]-proton shift reaction with a high chirality transfer, affording the corresponding rearranged products in acceptable yields. Without purification, these products were subjected to acid hydrolysis and the subsequent N-Cbz protection, providing the optically active tetrafluoroethylenated amides in moderate three-step yields.
Keywords: Tetrafluoroethylene fragment; optically active; amine; [1,3]-proton shift reaction
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Kabumoto, Y.; Yoshimoto, E.; Xiaohuan, B.; Yasui, M.; Yamada, S.; Konno, T. Beilstein Arch. 2024, 202451. doi:10.3762/bxiv.2024.51.v1
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