title: Asymmetric dearomatization of indoles through a Michael/Friedel-Crafts-type cascade to construct polycyclic spiroindolines.
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/Mg(II) 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.
authors: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China).
authors: Xiaohu
authors: X
authors: Zhao
authors: Xiaohua
authors: X
authors: Liu
authors: Hongjiang
authors: H
authors: Mei
authors: Jing
authors: J
authors: Guo
authors: Lili
authors: L
authors: Lin
authors: Xiaoming
authors: X
authors: Feng
mesh_terms: D002384:Catalysis; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis*; D007700:Kinetics; D008314:Malonates / Q000737:chemistry; D008352:Mannich Bases; D008968:Molecular Conformation; D011083:Polycyclic Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014961:X-Ray Diffraction
chemical_list: D007202:Indicators and Reagents; D007211:Indoles; D008314:Malonates; D008352:Mannich Bases; D011083:Polycyclic Compounds; C057812:indoline
keywords: aromaticity; asymmetric catalysis; cascade reactions; heterocycles; magnesium