Exploiting 3‐Methyleneisoindolinones as In Situ Generated Reactive Intermediates in the Synthesis of Tetrasubstituted Carbon Center

Beriša, Arben; Duplić, Filip; Purić, Marko; Gredičak, Matija; Topolovčan, Nikola (2025) Exploiting 3‐Methyleneisoindolinones as In Situ Generated Reactive Intermediates in the Synthesis of Tetrasubstituted Carbon Center. Asian Journal of Organic Chemistry, 14 (8). ISSN 2193-5807

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Abstract

In this study, we describe the operationally simple construction of a tetrasubstituted carbon center utilizing in situ formation of 3‐methyleneisoindolinones as reactive intermediates. An acid‐catalyzed Meyer–Schuster rearrangement of isoindolinone‐based propargylic alcohols followed by an intermolecular Friedel–Crafts alkylation assembles the 3,3‐disubstituted isoindolinones, an important architectural motif found in numerous biologically active compounds. Highly inert to structural changes in building blocks, this robust transformation allows the quick build‐up of a library of compounds with an embedded isoindolinone core. In addition, the in situ formation of the activated intermediate allows a selective installation of various structural characteristics

Item Type:	Article
Uncontrolled Keywords:	Acid catalyzed; Friedel–Crafts alkylation; Isoindolinones; Meyer–Schuster rearrangement; Tetrasubstituted carbon atom
Subjects:	NATURAL SCIENCES NATURAL SCIENCES > Chemistry 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:	Kristina Ciglar
Date Deposited:	04 Nov 2025 16:01
URI:	http://fulir.irb.hr/id/eprint/10139
DOI:	10.1002/ajoc.202500562

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