Influence of N ‐Substitution in 3‐Alkyl‐3‐hydroxyisoindolin‐1‐ones on the Stereoselectivity of Brønsted Acid‐Catalyzed Synthesis of 3‐Methyleneisoindolin‐1‐ones

Topolovčan, Nikola; Duplić, Filip; Gredičak, Matija (2021) Influence of N ‐Substitution in 3‐Alkyl‐3‐hydroxyisoindolin‐1‐ones on the Stereoselectivity of Brønsted Acid‐Catalyzed Synthesis of 3‐Methyleneisoindolin‐1‐ones. European Journal of Organic Chemistry, 2021 (28). pp. 3920-3924. ISSN 1434-193X

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Abstract

A comprehensive study on the influence of N -substitution on the stereoselective outcome of the synthesis of 3-methyleneisoindolin-1-ones from 3-alkyl-3-hydroxyisoindolin-1-ones is reported. The study was performed on an array of structurally diverse 3-alkyl-3-hydroxyisoindolin-1-ones with tunable sizes of N -substituents. In a methanesulfonic acid-catalyzed reaction, substrates without N -substituent (N-H) afforded exclusively the Z -isomer, while an increase in their size was followed by the formation of a stereoisomeric mixture with the E -isomer as the major component.

Item Type:	Article
Uncontrolled Keywords:	Catalysis; EnamidesN-Substitution; Stereoselectivity; Steric hindrance
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:	15 Dec 2021 10:49
URI:	http://fulir.irb.hr/id/eprint/6809
DOI:	10.1002/ejoc.202100400

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