State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300072, China.
Angew Chem Int Ed Engl. 2018 Mar 1;57(10):2653-2656. doi: 10.1002/anie.201712435. Epub 2018 Feb 6.
A highly efficient synthesis of enantioenriched spiroindolines by catalytic asymmetric dearomatization of indolyl dihydropyridines through a chiral phosphoric acid catalyzed enamine isomerization/spirocyclization/transfer hydrogenation sequence has been developed. This reaction proceeds under mild reaction conditions, affording novel spiroindolines in good yields (up to 88 %) with excellent enantioselectivity (up to 97 % ee). DFT calculations provide insights into the reaction mechanism as well as the origin of stereochemistry.
发展了一种通过手性磷酸催化的烯胺异构化/螺环化/转移氢化反应序列，高效合成对映体富集的螺吲哚啉的方法。该反应在温和的反应条件下进行，以良好的收率（高达 88%）和优异的对映选择性（高达 97%ee）得到新型螺吲哚啉。DFT 计算为反应机理以及立体化学的起源提供了深入的了解。
