The asymmetric synthesis of polycyclic 3-spirooxindole alkaloids via the cascade reaction of 2-isocyanoethylindoles.
- Resource Type
- Article
- Authors
- Zhao, Xiaohu; Liu, Xiaohua; Xiong, Qian; Mei, Hongjiang; Ma, Baiwei; Lin, Lili; Feng, Xiaoming
- Source
- Chemical Communications. 11/18/2015, Vol. 51 Issue 89, p16076-16079. 4p.
- Subject
- *OXINDOLES
*ALKALOIDS
*CATALYSTS
*CHEMICAL reactions
*CHEMICAL research
- Language
- ISSN
- 1359-7345
A highly enantioselective dearomative cascade reaction between 2-isocyanoethylindoles and 3-alkenyl-oxindoles was realized using a chiral N,N′-dioxide–Mg(ii) complex catalyst. This reaction provides a straightforward access to polycyclic 3-spirooxindoles bearing cyclopenta[b]indole units with four contiguous stereocenters in excellent yields and moderate to good stereoselectivities via a Michael/Friedel–Crafts/Mannich cascade. [ABSTRACT FROM AUTHOR]