Chiral N, N′‐Dioxide‐Zinc(II) Complex‐Catalyzed Asymmetric Aza‐Friedel–Crafts Reaction of Isatin‐Derived Ketimines with Indoles. Issue 19 (5th August 2016)

• Record Type: Journal Article
• Authors: Zhang, Xiying; Zhang, Jianlin; Lin, Lili; Zheng, Haifeng; Wu, Wangbin; Liu, Xiaohua; Feng, Xiaoming
• Is Part Of: Advanced synthesis & catalysis. Volume 358:Issue 19(2016)
• Page Start: 3021
• Page End: 3026
• Publication Date: 2016-08-05
• Subjects: asymmetric catalysis -- aza-Friedel-Crafts reaction -- N, N′-dioxides -- isatin-derived ketimines -- zinc(II); Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201600630
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A highly efficient chiral N, N′ ‐dioxide‐zinc(II) complex catalytic system has been developed for the enantioselective aza‐Friedel–Crafts reaction of isatin‐derived ketimines with indoles. A series of enantiomerically enriched 3‐indolyl‐3‐aminooxindoles containing a tetrasubstituted stereocenter were obtained in up to 99% yield with up to 96% ee . Furthermore, control experiments provide a fundamental sight into the mechanism of the reaction. Abstract :