Ni(ClO4)2-Catalyzed Friedel-Crafts Reaction of Coumarin-Fused Donor-Acceptor Cyclopropanes with Indoles: Stereoselective Synthesis of trans-3,4-Disubstituted-3,4-dihydrocoumarins

被引：14

作者：

Lee, Jusung ^{[1
]}

Ko, Kwang Min ^{[1
]}

Kim, Sung-Gon ^{[1
]}

机构：

[1] Kyonggi Univ, Dept Chem, 154-42 Gwanggyosan Ro, Suwon 16227, South Korea

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 30期

基金：

新加坡国家研究基金会;

关键词：

Earth-abundant metals; Friedel-Crafts reaction; Donor-acceptor cyclopropane; Heterocycles; Lewis acids; Synthetic methods; ONE-POT SYNTHESIS; CYCLIZATION CASCADE REACTION; ORTHO-QUINONE METHIDES; ASYMMETRIC-SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; O-HYDROXYCINNAMALDEHYDES; MICHAEL ADDITION; BRONSTED ACID; ENANTIOSELECTIVE SYNTHESIS; ORGANOBORONIC ACIDS;

D O I：

10.1002/ejoc.201800669

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective synthesis of trans-4-(3-indolylmethyl)-3,4-dihydrocoumarins has been developed. The method proceeds through a catalytic Friedel-Crafts reaction of coumarin-fused donor-acceptor cyclopropanes with indoles. The use of Ni(ClO4)(2) as a Lewis acid catalyst leads to the formation of a variety of 4-(3-indolylmethyl)-3,4-dihydrocoumarins in good yields with high diastereoselectivities.

引用

页码：4166 / 4170

页数：5

共 2 条

[1] Kinetic resolution of 4-substituted-3,4-dihydrocoumarins via Pd-catalyzed asymmetric allylic alkylation reaction: enantioselective synthesis of trans-3,4-disubstituted-3,4-dihydrocoumarins
Li, Xiao-Hui
Fang, Ping
Chen, Di
Hou, Xue-Long
ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (08): : 969 - 973
[2] Convenient synthesis of bis(indolyl)alkanes by dithiocarbohydrazone Schiff base/Zn(ClO4)2•6H2O catalyzed Friedel-Crafts reaction of indoles with imines
Hui, Yong-Hai
Chen, Yong-Cheng
Gong, Hai-Wei
Xie, Zheng-Feng
CHINESE CHEMICAL LETTERS, 2014, 25 (01) : 163 - 165

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