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

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‐a...

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Veröffentlicht in:Angewandte Chemie International Edition 2023-02, Vol.62 (8), p.e202217051-n/a
Hauptverfasser: Shen, Lulu, Zheng, Yin, Lin, Zitong, Qin, Tianzhu, Huang, Zhongxing, Zi, Weiwei
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Sprache:eng
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Zusammenfassung: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. 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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202217051