Asymmetric Dearomatization of Indoles through a Michael/Friedel–Crafts‐Type Cascade To Construct Polycyclic Spiroindolines |
| |
| Authors: | Xiaohu Zhao Prof Xiaohua Liu Hongjiang Mei Jing Guo Dr Lili Lin Prof Xiaoming Feng |
| |
| Institution: | 1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China);2. Collaborative Innovation Center of Chemical Science andEngineering, Tianjin (China) |
| |
| Abstract: | A highly efficient asymmetric dearomatization of indoles was realized through a cascade reaction between 2‐isocyanoethylindole and alkylidene malonates catalyzed by a chiral N,N′‐dioxide/MgII catalyst. Fused polycyclic indolines containing three stereocenters were afforded in good yields with excellent diastereo‐ and enantioselectivities through a Michael/Friedel–Crafts/Mannich cascade. When 2‐substituted 2‐isocyanoethylindoles were used, spiroindoline derivatives were obtained through a Michael/Friedel–Crafts reaction. |
| |
| Keywords: | aromaticity asymmetric catalysis cascade reactions heterocycles magnesium |
|
