N-Heterocyclic Carbene/Copper Cooperative Catalysis for the Asymmetric Synthesis of Spirooxindoles

被引：186

作者：

Zhang, Zi-Jing ^{[1
,2
]}

Zhang, Ling ^{[1
,2
]}

Geng, Rui-Long ^{[1
,2
]}

Song, Jin ^{[1
,2
]}

Chen, Xiao-Hua ^{[3
]}

Gong, Liu-Zhu ^{[1
,2
,4
]}

机构：

[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Anhui, Peoples R China

[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China

[4] Chinese Acad Sci, Ctr Excellence Mol Synth, Hefei 230026, Anhui, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 35期

关键词：

cooperative catalysis; copper; enals; N-heterocyclic carbenes; spirooxindoles; ISATIN-DERIVED ENALS; ENANTIOSELECTIVE SYNTHESIS; SYNERGISTIC CATALYSIS; DUAL CATALYSIS; 3+3 ANNULATION; NHC CATALYSIS; ACCESS; ORGANOCATALYSIS; ALLYLATION; SCAFFOLDS;

D O I：

10.1002/anie.201907188

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Highly enantioselective [3+3] and [3+4] annulations of isatin-derived enals with ethynylethylene carbonates and ethynyl benzoxazinanones are enabled by NHC/cooper cooperative catalysis, leading to a big library of spirooxindole derivatives in high structural diversity and enantioselectivity (up to 99 % ee). Both reactions represent a nicely synergistic integration of NHC and copper catalysis, in which both catalysts activate the substrates and the chiral NHC perfectly controls the stereochemistry.

引用

页码：12190 / 12194

页数：5

共 83 条

[1] Combinations of Aminocatalysts and Metal Catalysts: A Powerful Cooperative Approach in Selective Organic Synthesis [J].

Afewerki, Samson ;

Cordova, Armando .

CHEMICAL REVIEWS, 2016, 116 (22) :13512-13570

[2] Synergistic catalysis: A powerful synthetic strategy for new reaction development [J].

Allen, Anna E. ;

MacMillan, David W. C. .

CHEMICAL SCIENCE, 2012, 3 (03) :633-658

[3]

[Anonymous], 2018, ANGEW CHEM-GER EDIT

[4]

Bai YG, 2014, CHEM COMMUN, V50, P13391, DOI [10.1039/c4cc06111j, 10.1039/C4CC06111J]

[5] Dual-function Pd/NHC catalysis: tandem allylation-isomerization-conjugate addition that allows access to pyrroles, thiophenes and furans [J].

Bai, Yaguang ;

Xiang, Shaohua ;

Leow, Min Li ;

Liu, Xue-Wei .

CHEMICAL COMMUNICATIONS, 2014, 50 (46) :6168-6170

[6] Transition-Metal-Catalyzed Functionalization of Propargylic Alcohols and Their Derivatives [J].

Bauer, Eike B. .

SYNTHESIS-STUTTGART, 2012, 44 (08) :1131-1151

[7] Development of Synthetic Methodologies via Catalytic Enantioselective Synthesis of 3,3-Disubstituted Oxindoles [J].

Cao, Zhong-Yan ;

Zhou, Feng ;

Zhou, Jian .

ACCOUNTS OF CHEMICAL RESEARCH, 2018, 51 (06) :1443-1454

[8] Asymmetric Organocatalysis Combined with Metal Catalysis: Concept, Proof of Concept, and Beyond [J].

Chen, Dian-Feng ;

Han, Zhi-Yong ;

Zhou, Xiao-Le ;

Gong, Liu-Zhu .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (08) :2365-2377

[9] Asymmetric Catalytic [4+2] Cycloaddition via Cu-Allenylidene Intermediate: Stereoselective Synthesis of Tetrahydroquinolines Fused with a γ-Lactone Moiety [J].

Chen, Hao ;

Lu, Xuehe ;

Xia, Xuejian ;

Zhu, Qiongqiong ;

Song, Yanhong ;

Chen, Jie ;

Cao, Weiguo ;

Wu, Xiaoyu .

ORGANIC LETTERS, 2018, 20 (07) :1760-1763

[10] Enantioselective β-Protonation of Enals via a Shuttling Strategy [J].

Chen, Jiean ;

Yuan, Pengfei ;

Wang, Leming ;

Huang, Yong .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (20) :7045-7051

← 1 2 3 4 5 6 7 8 9 →