Asymmetric Dearomatization of Indoles through a Michael/Friedel-Crafts-Type Cascade To Construct Polycyclic Spiroindolines

被引：160

作者：

Zhao, Xiaohu ^{[1
]}

Liu, Xiaohua ^{[1
]}

Mei, Hongjiang ^{[1
]}

Guo, Jing ^{[1
]}

Lin, Lili ^{[1
]}

Feng, Xiaoming ^{[1
,2
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

[2] Collaborat Innovat Ctr Chem Sci and Engn, Tianjin, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 13期

基金：

中国国家自然科学基金;

关键词：

aromaticity; asymmetric catalysis; cascade reactions; heterocycles; magnesium; ENANTIOSELECTIVE TOTAL-SYNTHESIS; ALLYLIC DEAROMATIZATION; MULTICOMPONENT REACTIONS; NATURAL-PRODUCTS; DERIVATIVES; PYRROLOINDOLINES; ACCESS; CYCLIZATION; ALKYLATION; ALKALOIDS;

D O I：

10.1002/anie.201410814

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：4032 / 4035

页数：4

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