Copper-Catalyzed Enantioselective C1,N-Dipolar (3+2) Cycloadditions of 2-Aminoallyl Cations with Indoles

被引：32
|
作者：
Shen, Lulu [1 ,2 ]
Zheng, Yin [3 ]
Lin, Zitong [1 ,2 ]
Qin, Tianzhu [1 ,2 ]
Huang, Zhongxing [3 ]
Zi, Weiwei [1 ,2 ,4 ]
机构：
[1] Nankai Univ, Coll Chem, State Key Lab, Tianjin 300071, Peoples R China
[2] Nankai Univ, Inst Elementoorgan Chem, Coll Chem, Tianjin 300071, Peoples R China
[3] Univ Hong Kong, Dept Chem, State Key Lab Synthet Chem, Hong Kong, Peoples R China
[4] Haihe Lab Sustainable Chem Transformat, Tianjin 300071, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 08期
基金：
国家重点研发计划;
关键词：
1; 3-Dipoles; Allyl Cations; Copper Catalysis; Cycloaddition; Enantioselectivity; ASYMMETRIC 4+3 CYCLOADDITIONS; OXYALLYL CATIONS; PROPARGYLIC ESTERS; BETA-KETOESTERS; CONSTRUCTION; ANNULATION; KETONES; PYRROLOINDOLINES; ACTIVATION; 1,3-DIENES;
D O I：
10.1002/anie.202217051
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
2-Aminoallyl cations are versatile 1,3-dipoles that could potentially be used for diverse (3+n) cycloaddition reactions. Despite some preliminary studies, the asymmetric catalytic transformation of these species is still underdeveloped. We herein report a binuclear copper-catalyzed generation of 2-aminoallyl cations from ethynyl methylene cyclic carbamates and their enantioselective (3+2) cycloaddition reaction with indoles to construct chiral pyrroloindolines. This transformation features a novel C1,N-dipolar reactivity for 2-aminoallyl cations.
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页数：6
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