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Influence of N ‐Substitution in 3‐Alkyl‐3‐hydroxyisoindolin‐1‐ones on the Stereoselectivity of Brønsted Acid‐Catalyzed Synthesis of 3‐Methyleneisoindolin‐1‐ones
Author(s) -
Topolovčan Nikola,
Duplić Filip,
Gredičak Matija
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100400
Subject(s) - methanesulfonic acid , chemistry , stereoselectivity , alkyl , substituent , catalysis , brønsted–lowry acid–base theory , substitution (logic) , stereochemistry , medicinal chemistry , organic chemistry , computer science , programming language
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.