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

Ronald Grigg*, H. Q.Nimal Gunaratne, Visuvanathar Sridharan

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

41 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1183-1184
Number of pages2
JournalJournal of the Chemical Society, Chemical Communications
Issue number17
DOIs
Publication statusPublished - 1985

Bibliographical note

Copyright:
Copyright 2019 Elsevier B.V., All rights reserved.

ASJC Scopus subject areas

  • Molecular Medicine

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