Unprecedented regio and stereocontrol in Povarov reaction ofbenzylidene-(3-nitrophenyl)amine

Paul J. Stevenson*, Isla Graham

*Corresponding author for this work

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Typically, Povarov reactions of imines derived from aromatic amines and aromatic aldehydes show poor exo/endo-stereoselectivity and to date no data is available on the regioselectivity of the cyclisation when 3-substituted imines are employed. We have demonstrated that reaction using acyclic enamides as the alkene component with 3-nitro substituted imines is completely regioselective and gave only the 5-nitro substituted tetrahydroquinoline. As a bonus the reaction also became completely exo-selective with the stereochemistry of the E-alkene preserved in the tetrahydroquinoline product.

Original languageEnglish
Pages (from-to)139-144
Number of pages6
JournalArkivoc
Volume2003
Issue number7
Publication statusPublished - 01 Dec 2003

Keywords

  • Imines
  • Povarov reaction
  • Regioselective
  • Tetrahydroquinolines
  • Yttrium triflate

ASJC Scopus subject areas

  • Organic Chemistry

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