Topolovčan, Nikola; Degač, Marina; Čikoš, Ana; Gredičak, Matija (2022) Chemoselective and Regioselective Synthesis of Spiroisoindolinone Indenes via an Intercepted Meyer-Schuster Rearrangement/Intramolecular Friedel-Crafts Alkylation Relay. Journal of Organic Chemistry, 87 . pp. 3712-3717. ISSN 0022-3263
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Abstract
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.
Item Type: | Article | ||||||||
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Uncontrolled Keywords: | spiroisoindolinone indenes ; Meyer−Schuster rearrangement | ||||||||
Subjects: | NATURAL SCIENCES > Chemistry > Organic Chemistry | ||||||||
Divisions: | Division of Organic Chemistry and Biochemistry | ||||||||
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Depositing User: | Matija Gredičak | ||||||||
Date Deposited: | 31 Mar 2022 11:46 | ||||||||
URI: | http://fulir.irb.hr/id/eprint/7134 | ||||||||
DOI: | 10.1021/acs.joc.1c02647 |
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