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

A Brønsted
acid-catalyzed reaction between isoindolinone-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.