基于[1,3]-质子转移反应获取光学活性四氟乙烯化胺。
Access to optically active tetrafluoroethylenated amines based on [1,3]-proton shift reaction.
作者信息
Kabumoto Yuta, Yoshimoto Eiichiro, Xiaohuan Bing, Morita Masato, Yasui Motohiro, Yamada Shigeyuki, Konno Tsutomu
机构信息
Faculty of Molecular Chemistry and Engineering, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan.
Department of Materials Science and Engineering, Graduate School of Science and Engineering, Ibaraki University, 4-12-1 Nakanarusawa, Hitachi, Ibaraki 316-8511, Japan.
出版信息
Beilstein J Org Chem. 2024 Nov 1;20:2776-2783. doi: 10.3762/bjoc.20.233. eCollection 2024.
Treatment of various ()--(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 -Cbz protection, providing the optically active tetrafluoroethylenated amides in moderate three-step yields.
在室温至50°C下，将各种()-(2,2,3,3-四氟戊-4-亚烯基)-1-苯乙胺衍生物与2.4当量的DBU在甲苯中反应24小时，可顺利发生[1,3]-质子转移反应，并具有高的手性转移，以可接受的产率得到相应的重排产物。这些产物无需纯化，直接进行酸水解和随后的-Cbz保护，以适度的三步产率得到光学活性的四氟乙烯化酰胺。
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