Shen Lulu, Zheng Yin, Lin Zitong, Qin Tianzhu, Huang Zhongxing, Zi Weiwei
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071, P. R. China.
State Key Laboratory of Synthetic Chemistry, Department of Chemistry, University of Hong Kong, Hong Kong, P. R. China.
Angew Chem Int Ed Engl. 2023 Feb 13;62(8):e202217051. doi: 10.1002/anie.202217051. Epub 2023 Jan 18.
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.
2-氨基烯丙基阳离子是通用的1,3-偶极体，可潜在地用于各种(3+n)环加成反应。尽管有一些初步研究，但这些物种的不对称催化转化仍未得到充分发展。我们在此报告了一种双核铜催化的从乙炔基亚甲基环氨基甲酸酯生成2-氨基烯丙基阳离子及其与吲哚的对映选择性(3+2)环加成反应，以构建手性吡咯并吲哚啉。这种转化具有2-氨基烯丙基阳离子的新型C1,N-偶极反应性。
