Wang Xin-Wei, Li Xiang, Chen Mu-Wang, Wu Bo, Zhou Yong-Gui
State Key Laboratory of Fine Chemicals, Zhang Dayu School of Chemistry, Dalian University of Technology, Dalian 116024, P. R. China.
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, P. R. China.
J Org Chem. 2021 May 7;86(9):6897-6906. doi: 10.1021/acs.joc.1c00289. Epub 2021 Apr 12.
Chiral phosphoric acid-catalyzed Pictet-Spengler reactions of 2-(1-indolyl)aniline derivatives and isatins by the condensation/cyclization process have been realized. A series of enantioenriched 5',11'-dihydrospiro[indoline-3,6'-indolo[3,2-]quinolin]-2-ones bearing quaternary stereogenic centers were obtained with excellent yields and up to >99% ee. This protocol was suitable for the Pictet-Spengler reactions of 2-(1-benzyl-5-methyl-1-pyrrol-2-yl)aniline, and a variety of 1',5'-dihydro-spiro[indoline-3,4'-pyrrolo[3,2-]quinolin]-2-ones could also be obtained in good yields and up to 88% ee.
通过缩合/环化过程实现了手性磷酸催化的2-(1-吲哚基)苯胺衍生物与异吲哚酮的Pictet-Spengler反应。获得了一系列带有季碳立体中心的对映体富集的5',11'-二氢螺[吲哚啉-3,6'-吲哚并[3,2-]喹啉]-2-酮，产率优异，对映体过量率高达>99%。该方法适用于2-(1-苄基-5-甲基-1-吡咯-2-基)苯胺的Pictet-Spengler反应，也可以以良好的产率和高达88%的对映体过量率获得多种1',5'-二氢螺[吲哚啉-3,4'-吡咯并[3,2-]喹啉]-2-酮。
