通过2-异氰基乙基吲哚的串联反应实现多环3-螺氧化吲哚生物碱的不对称合成。
The asymmetric synthesis of polycyclic 3-spirooxindole alkaloids via the cascade reaction of 2-isocyanoethylindoles.
作者信息
Zhao Xiaohu, Liu Xiaohua, Xiong Qian, Mei Hongjiang, Ma Baiwei, Lin Lili, Feng Xiaoming
机构信息
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China.
出版信息
Chem Commun (Camb). 2015 Nov 18;51(89):16076-9. doi: 10.1039/c5cc06353a.
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.
使用手性N,N'-二氧化物-Mg(II)配合物催化剂实现了2-异氰基乙基吲哚与3-烯基氧化吲哚之间的高度对映选择性脱芳构化串联反应。该反应通过迈克尔/傅克/曼尼希串联反应，以优异的产率和中等至良好的立体选择性，直接合成了带有环戊并[b]吲哚单元且具有四个相邻立体中心的多环3-螺氧化吲哚。
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