Asymmetric Dearomatization of Indoles through a Michael/Friedel-Crafts-Type Cascade To Construct Polycyclic Spiroindolines
Asymmetric Dearomatization of Indoles through a Michael/Friedel-Crafts-Type Cascade To Construct Polycyclic Spiroindolines
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通过 Michael/Friedel-Crafts 型级联对吲哚进行不对称脱芳构化构建多环螺吲哚啉
DOI：
10.1002/anie.201410814
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发表时间：
2015
期刊：
影响因子：
--
通讯作者：
Xiaoming Feng
中科院分区：
文献类型：
--
作者：
Xiaohu Zhao;Xiaohua Liu;Hongjiang Mei;Jing Guo;Lili Lin;Xiaoming Feng
采用手性N，N′-二氧化物/Mg Ⅱ催化剂，通过2-异氰乙基吲哚和烷叉丙二酸酯的级联反应实现了吲哚的高效不对称脱芳构化.通过Michael/Friedel-Crafts/Mannich级联反应，以良好的产率和优异的非对映体和对映体选择性得到含有三个立体中心的稠合多环吲哚啉。当使用2-取代的2-异氰酰基乙基吲哚时，通过迈克尔/弗里德-克拉夫茨反应获得螺吲哚啉衍生物。
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/MgIIcatalyst. 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.