Au(I)-Catalyzed Domino Cyclization of 1,6-Diynes Incorporated with Indole
Guzhou Chen, Peng‐Yu Liu, Huanhuan Zou, Jiadong Hu, Xiaowu Fang, Dongyang Xu, Yu‐Peng He, Hongbo Wei, Weiqing Xie
Abstract
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.
Topics & Concepts
DominoChemistryIndole testChemoselectivityAlkyneCatalysisCombinatorial chemistryCascade reactionStereochemistryCascadeOrganic chemistryChromatographyCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsSynthetic Organic Chemistry Methods