Enantioselective synthesis of dihydrocoumarin derivatives by chiral scandium(III)-complex catalyzed inverse-electron-demand hetero-Diels-Alder reaction

被引：107

作者：

Hu, Haipeng ^{[1
]}

Liu, Yangbin ^{[1
]}

Guo, Jing ^{[1
]}

Lin, Lili ^{[1
]}

Xu, Yali ^{[1
]}

Liu, Xiaohua ^{[1
]}

Feng, Xiaoming ^{[1
,2
]}

机构：

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

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

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 18期

基金：

中国国家自然科学基金;

关键词：

QUINONE-METHIDES; ASYMMETRIC-SYNTHESIS; CYCLOADDITION; AZLACTONES; CHEMISTRY; LIGANDS; ROUTE;

D O I：

10.1039/c4cc10343b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An asymmetric inverse-electron-demand hetero-Diels-Alder reaction between o-quinone methides and azlactones to generate potentially pharmacological active dihydrocoumarins has been achieved efficiently by using a chiral N,N'-dioxide-Sc(III) complex as the catalyst. The desired products were obtained in high yields with excellent enantioselectivities and diastereoselectivities (up to 94% yield, 96% ee and >19 : 1 dr) under mild reaction conditions. A concerted reaction pathway was confirmed by Operando IR and control experiments.

引用

页码：3835 / 3837

页数：3

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