Synergistic Sc(III)/Au(I)-Catalyzed Dearomative Spiroannulation of 2‑(Ethynyl)aryl Cyclopropanes with 2‑Aryl Indoles

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...

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Published inOrganic letters Vol. 24; no. 47; pp. 8709 - 8713
Main Authors Xiao, Jun-An, Peng, Hai, Zhang, Huan, Meng, Ru-Fang, Lin, Chenxiang, Su, Wei, Huang, Yanmin
Format Journal Article
LanguageEnglish
Published American Chemical Society 02.12.2022
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Summary: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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c03679