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

SM Allin, CJ Northfield, MI Page, Alexandra Martha Zoya Slawin

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57 Citations (Scopus)

Abstract

New methodology for the synthesis of non-racemic isoindolinone targets has been developed through application of tricyclic gamma-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.

Original languageEnglish
Pages (from-to)1715-1721
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number11
DOIs
Publication statusPublished - 2000

Keywords

  • HIGHLY DIASTEREOSELECTIVE SYNTHESIS
  • ENANTIOSELECTIVE TOTAL SYNTHESES
  • HIV-1 REVERSE-TRANSCRIPTASE
  • SIMPLE ASYMMETRIC-SYNTHESIS
  • 2-SUBSTITUTED PYRROLIDINES
  • PRECURSORS
  • INHIBITORS
  • LACTAMS

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