4770-29-0Relevant academic research and scientific papers
Influence of N-Substitution in 3-Alkyl-3-hydroxyisoindolin-1-ones on the Stereoselectivity of Br?nsted Acid-Catalyzed Synthesis of 3-Methyleneisoindolin-1-ones
Topolov?an, Nikola,Dupli?, Filip,Gredi?ak, Matija
supporting information, p. 3920 - 3924 (2021/08/24)
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.
