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Chemoselective and Regioselective Synthesis of Spiroisoindolinone Indenes via an Intercepted Meyer-Schuster Rearrangement/Intramolecular Friedel-Crafts Alkylation Relay (CROSBI ID 307825)

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Topolovčan, Nikola ; Degač, Marina ; Čikoš, Ana ; Gredičak, Matija Chemoselective and Regioselective Synthesis of Spiroisoindolinone Indenes via an Intercepted Meyer-Schuster Rearrangement/Intramolecular Friedel-Crafts Alkylation Relay // Journal of organic chemistry, 87 (2022), 3712-3717. doi: 10.1021/acs.joc.1c02647

Podaci o odgovornosti

Topolovčan, Nikola ; Degač, Marina ; Čikoš, Ana ; Gredičak, Matija

engleski

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.

Acid-catalyzed reactions ; Aromatic nucleophiles ; Chemoselective ; Friedel-Crafts alkylation ; Higher yield ; Intramolecular friedel-crafts ; Isoindolinone ; Meyer-Schuster rearrangement ; Propargylic alcohols ; Regioselective synthesis

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Podaci o izdanju

87

2022.

3712-3717

objavljeno

0022-3263

1520-6904

10.1021/acs.joc.1c02647

Povezanost rada

Kemija

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