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

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
Uncontrolled Keywords: spiroisoindolinone indenes ; Meyer−Schuster rearrangement
Subjects: NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Projects:
Project titleProject leaderProject codeProject type
Nove strategije za pripravu tetrasupstituiranih kiralnih centara: asimetrične katalitičke reakcije usmjerene protuanionom-NSYNC-ACDCMatija GredičakIP-2018-01-4053HRZZ
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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