A simple one-step synthesis of N-substituted isoindolin-1-ones. Diastereofacially selective protonation of an intermediate isoindolinol

R Grigg, HQN Gunaratne, V Sridharan

Index: Grigg, Ronald; Gunaratne, H. Q. Nimal; Sridharan, Visuvanathar Journal of the Chemical Society, Chemical Communications, 1985 , # 17 p. 1183 - 1184

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Citation Number: 30

Abstract

α-Amino acids and their methyl esters, arylamines, heterocyclic amines and, less efficiently, aryl substituted aliphatic amines, react with o-phthaldialdehyde in the presence of acetic acid to give N-substituted isoindolin-1-ones in excellent yield; deuteriation studies implicate an isoindolinol intermediate and, when α-amino acids are used, provide evidence of its diastereofacially selective protonation.