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Au(I)-Catalyzed Domino Cyclization of 1,6-Diynes Incorporated with Indole

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journal contribution
posted on 05.03.2021, 20:04 by Guzhou Chen, Peng-Yu Liu, Huanhuan Zou, Jiadong Hu, Xiaowu Fang, Dongyang Xu, Yu-Peng He, Hongbo Wei, Weiqing Xie
We disclose herein a Au­(I)-catalyzed domino cyclization of 1,6-diynes incorporated with indole. This protocol enabled the diastereoselective buildup of indole-fused azabicyclo[3.3.1]­nonanes from linear precursors. Density functional theory calculations showed that the reaction proceeded via an unprecedented cascade dearomatization/rearomatization/dearomatization process. Independent gradient model analysis revealed that a noncovalent attractive interaction between the distal alkyne and the Au/proximal complex was responsible for the chemoselectivity of the first spirocyclization step.