Copper-Catalyzed Enantioselective C1,N-Dipolar (3+2) Cycloadditions of 2-Aminoallyl Cations with Indoles
Lulu Shen
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 P. R. China
Search for more papers by this authorDr. Yin Zheng
State Key Laboratory of Synthetic Chemistry, Department of Chemistry, University of Hong Kong, Hong Kong, P. R. China
Search for more papers by this authorZitong Lin
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 P. R. China
Search for more papers by this authorTianzhu Qin
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 P. R. China
Search for more papers by this authorProf. Dr. Zhongxing Huang
State Key Laboratory of Synthetic Chemistry, Department of Chemistry, University of Hong Kong, Hong Kong, P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Weiwei Zi
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 P. R. China
Haihe Laboratory of Sustainable Chemical Transformations, Tianjin, 300071 China
Search for more papers by this authorLulu Shen
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 P. R. China
Search for more papers by this authorDr. Yin Zheng
State Key Laboratory of Synthetic Chemistry, Department of Chemistry, University of Hong Kong, Hong Kong, P. R. China
Search for more papers by this authorZitong Lin
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 P. R. China
Search for more papers by this authorTianzhu Qin
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 P. R. China
Search for more papers by this authorProf. Dr. Zhongxing Huang
State Key Laboratory of Synthetic Chemistry, Department of Chemistry, University of Hong Kong, Hong Kong, P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Weiwei Zi
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 P. R. China
Haihe Laboratory of Sustainable Chemical Transformations, Tianjin, 300071 China
Search for more papers by this authorGraphical Abstract
A binuclear copper-catalyzed (3+2) cycloaddition of 2-aminoallyl cations with indoles was achieved. This transformation featured a unique C1,N-dipolar cycloaddition reactivity for 2-aminoallyl cations. Enantioenriched pyrroloindoline derivatives were prepared by this cycloaddition in high yields with good enantio- and diastereoselectivities.
Abstract
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.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the supplementary material of this article.
Supporting Information
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| anie202217051-sup-0001-misc_information.pdf11.5 MB | Supporting Information |
| anie202217051-sup-0001-SI_checkcif.pdf164.6 KB | Supporting Information |
| anie202217051-sup-0001-SI_cu_1117_6_0m.cif1.1 MB | Supporting Information |
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