Chemoselective and Regioselective Synthesis of Spiroisoindolinone Indenes via an Intercepted Meyer-Schuster Rearrangement/Intramolecular Friedel-Crafts Alkylation Relay

A Bronsted acid-catalyzed reaction between iso-indolinone-derived propargylic alcohols and external aromatic nucleophiles for the construction of spiroisoindolinone indenes is described. The reaction proceeds rapidly with a broad range of substrates to generate spiroindenes chemoselectively and regioselectively in moderate to high yields. Key to the success of this transformation is an intercepted Meyer-Schuster rearrangement/intramolecular Friedel-Crafts alkylation relay that offers a modular approach in the synthesis of target compounds.

Automated summary

The construction of spiroisoindolinone indenes through a Bronsted acid-catalyzed reaction between iso-indolinone-derived propargylic alcohols and external aromatic nucleophiles is described. The reaction offers a modular approach for the synthesis of target compounds through an intercepted Meyer-Schuster rearrangement/intramolecular Friedel-Crafts alkylation relay, providing spiroindenes with good chemoselectivity and regioselectivity in moderate to high yields.