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Liu, Qiong‐Jie; Zhu, Jun; Song, Xiang‐Yang; Wang, Lijia; Wang, Sunewang R.; Tang, Yong
Angewandte Chemie International Edition, March 26, 2018, Letnik: 57, Številka: 14Journal Article
A facile and efficient method to produce optically pure benzofuroindolines, especially those without 3‐substituents that are susceptible to rearomatization, through 3+2 annulation of indoles with quinones is described. The suitable combination of a BOX ligand CuII hydrate complex and freshly activated molecular sieves functions to give controllably dynamic release of water, which enables the success of this reaction. This reaction can be performed on a gram scale with only 0.5 mol % catalyst loading. Thinking outside the BOX: A CuII‐catalyzed asymmetric 3+2 annulation of indoles with quinones provides diverse access to the optically pure benzofuroindolines, including those without 3‐substituents that are susceptible to rearomatization, for the first time. The use of a BOX ligand copper hydrate complex in combination with activated molecular sieves for the controlled release of H2O leads to reproducibly high yields and excellent enantioselectivity.
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