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

被引：108

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

共 50 条

[21] Synthesis of Annulated Pyridines by Intramolecular Inverse-Electron-Demand Hetero-Diels-Alder Reaction under Superheated Continuous Flow Conditions
Martin, Rainer E.
Morawitz, Falk
Kuratli, Christoph
Alker, Andre M.
Alanine, Alexander I.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (01) : 47 - 52
[22] N,N′-Dioxide/Nickel(II)-Catalyzed Asymmetric Inverse-Electron-Demand Hetero-Diels-Alder Reaction of β,γ-Unsaturated α-Ketoesters with Enecarbamates
Zhou, Yuhang
Zhu, Yin
Lin, Lili
Zhang, Yulong
Zheng, Jianfeng
Liu, Xiaohua
Feng, Xiaoming
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (50) : 16753 - 16758
[23] The N,N′-dioxide/Ni(II)-catalyzed asymmetric inverse-electron-demand hetero-Diels-Alder reaction of methyleneindolinones with hetero-substituted alkenes
Zhou, Yuhang
Lin, Lili
Yin, Chengkai
Wang, Zhengmeng
Liu, Xiaohua
Feng, Xiaoming
CHEMICAL COMMUNICATIONS, 2015, 51 (58) : 11689 - 11692
[24] A chiral scandium-complex-catalyzed asymmetric inverse-electron-demand oxa-Diels-Alder reaction of o-quinone methides with fulvenes
Zhang, Jianlin
Lin, Lili
He, Changqiang
Xiong, Qian
Liu, Xiaohua
Feng, Xiaoming
CHEMICAL COMMUNICATIONS, 2018, 54 (01) : 74 - 77
[25] FUNCTIONALLY SUBSTITUTED PYRIDINES BY HETERO-DIELS-ALDER REACTION WITH INVERSE ELECTRON DEMAND
HAAGZEINO, B
MAIER, ME
SCHMIDT, RR
CHEMISCHE BERICHTE-RECUEIL, 1987, 120 (09): : 1505 - 1509
[26] Inverse electron demand hetero-Diels-Alder reaction of o-quinones
Zhang, Jinsong
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
[27] Enantioselective direct aza hetero-Diels-Alder reaction catalyzed by chiral Bronsted acids
Liu, Hua
Cun, Lin-Feng
Mi, Ai-Qiao
Jiang, Yao-Zhong
Gong, Liu-Zhu
ORGANIC LETTERS, 2006, 8 (26) : 6023 - 6026
[28] Copper-Catalyzed Enantioselective Inverse Electron-Demand Hetero-Diels-Alder Reactions of Diazadienes with Enol Ethers: Efficient Synthesis of Chiral Pyridazines
Gao, Shuang
Chen, Jia-Rong
Hu, Xiao-Qiang
Cheng, Hong-Gang
Lu, Liang-Qiu
Xiao, Wen-Jing
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (18) : 3539 - 3544
[29] Chiral phosphoric acid catalyzed enantioselective inverse-electron-demand oxa-Diels-Alder reactions to synthesize chiral tricyclic tetrahydropyran derivatives
Tang, Cong-Yun
Wu, Jie
Ji, Feng-Ting
Tian, Fang
Peng, Lin
Wang, Liang-Liang
ORGANIC CHEMISTRY FRONTIERS, 2023, 11 (01) : 211 - 216
[30] Chiral gold complex-catalyzed hetero-diels-alder reaction of diazenes: Highly enantioselective and general for dienes
Gong, L.-Z. (gonglz@ustc.edu.cn), 1600, American Chemical Society (135):

← 1 2 3 4 5 →