Approaches to the synthesis of non-racemic 3-substituted isoindolinone derivatives

Steven M. Allin, Christopher J. Northfield, Michael I. Page, Alexandra M.Z. Slawin

Research output: Contribution to journalArticle

50 Citations (Scopus)

Abstract

New methodology for the synthesis of non-racemic isoindolinone targets has been developed through application of tricyclic γ-lactam substrates as N-acyliminium ion precursors in reactions with carbon and hydride nucleophiles. Removal of the phenylglycinol derived chiral auxiliary can be achieved without loss of stereochemical integrity at the newly created asymmetric centre, and we report a novel method for this key step using conc. sulfuric acid.

LanguageEnglish
Pages1715-1721
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number11
DOIs
Publication statusPublished - 2000

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Lactams
Nucleophiles
Hydrides
Carbon
Ions
Derivatives
Substrates
N-phenylethanolamine
sulfuric acid

Cite this

Allin, Steven M. ; Northfield, Christopher J. ; Page, Michael I. ; Slawin, Alexandra M.Z. / Approaches to the synthesis of non-racemic 3-substituted isoindolinone derivatives. In: Journal of the Chemical Society, Perkin Transactions 1. 2000 ; No. 11. pp. 1715-1721.
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Approaches to the synthesis of non-racemic 3-substituted isoindolinone derivatives. / Allin, Steven M.; Northfield, Christopher J.; Page, Michael I.; Slawin, Alexandra M.Z.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 11, 2000, p. 1715-1721.

Research output: Contribution to journalArticle

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