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 regio...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-03, Vol.87 (5), p.3712-3717
Main Authors: Topolovčan, Nikola, Degač, Marina, Čikoš, Ana, Gredičak, Matija
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c02647