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

Lulu Shen; Yin Zheng; Zitong Lin; Tianzhu Qin; Zhongxing Huang; Weiwei Zi

doi:10.1002/anie.202217051

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

Angew Chem Int Ed Engl. 2023 Feb 13;62(8):e202217051. doi: 10.1002/anie.202217051. Epub 2023 Jan 18.

Authors

Lulu Shen¹, Yin Zheng², Zitong Lin¹, Tianzhu Qin¹, Zhongxing Huang², Weiwei Zi^{1

3}

Affiliations

¹ State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071, P. R. China.
² State Key Laboratory of Synthetic Chemistry, Department of Chemistry, University of Hong Kong, Hong Kong, P. R. China.
³ Haihe Laboratory of Sustainable Chemical Transformations, Tianjin, 300071, China.

PMID: 36562702
DOI: 10.1002/anie.202217051

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.

Keywords: 1,3-Dipoles; Allyl Cations; Copper Catalysis; Cycloaddition; Enantioselectivity.

Abstract

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