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

被引：177

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

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