Asymmetric Dearomatization of Indoles through a Michael/Friedel–Crafts‐Type Cascade To Construct Polycyclic Spiroindolines1. (3rd February 2015)

• Record Type: Journal Article
• Authors: Zhao, Xiaohu; Liu, Xiaohua; Mei, Hongjiang; Guo, Jing; Lin, Lili; Feng, Xiaoming
• Is Part Of: Angewandte Chemie. Volume 127:Number 13(2015)
• Page Start: 4104
• Page End: 4107
• Publication Date: 2015-02-03
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201410814
• Languages: English
• ISSNs: 0044-8249

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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.</p> </abstract>