engleski

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

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.

Catalysis ; EnamidesN-Substitution ; Stereoselectivity ; Steric hindrance

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