Gold-Catalyzed Intramolecular Dearomatization Reactions of Indoles for the Synthesis of Spiroindolenines and Spiroindolines.

Org Lett

State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis , Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 LinglingLu , Shanghai 200032 , China.

Published: February 2020

A gold-catalyzed dearomatization reaction of indole derivatives was realized in the presence of JohnPhosAuCl/AgOMs to afford a series of spiroindolenines in excellent yields (≤99%). In addition, when the Hantzsch ester was used as the hydrogen transfer reagent, various spiroindolines were obtained in a cascade fashion starting from readily available indole derivatives in modest to good yields (≤79%). Both reactions feature readily available substrates, mild conditions, and good functional group tolerance.

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http://dx.doi.org/10.1021/acs.orglett.9b03988DOI Listing

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