Synergistic Sc(III)/Au(I)-Catalyzed Dearomative Spiroannulation of 2-(Ethynyl)aryl Cyclopropanes with 2-Aryl Indoles
Jun‐An Xiao, Hai Peng, Huan Zhang, Ru‐Fang Meng, Chenxiang Lin, Wei Su, Yanmin Huang
Abstract
The diastereoselective assembly of spiroindolenines via a synergistic scandium/gold-catalyzed dearomative spiroannulation is herein described. This protocol offers access to a wide variety of spiroindolenine derivatives in 86% average yield with moderate to excellent diastereoselectivities (up to 97:3 dr). The control experimental studies lend support to the bimetallic relay catalysis. Moreover, the scale-up reaction and synthetic transformations of spiroindolenine product further demonstrate its synthetic utility.
Topics & Concepts
ChemistryBimetallic stripArylCatalysisScandiumCombinatorial chemistryYield (engineering)Reaction conditionsSynergistic catalysisMedicinal chemistryOrganic chemistryMaterials scienceMetallurgyAlkylCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions