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 title Project leader Project code Project type Nove strategije za pripravu tetrasupstituiranih kiralnih centara: asimetrične katalitičke reakcije usmjerene protuanionom-NSYNC-ACDC Matija Gredičak IP-2018-01-4053 HRZZ
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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