An investigation of (R)-(+)-1-(1-naphthyl)ethylimines and (R)-(+)-1-(phenyl)ethylimines as chiral templates in the staudinger reaction

Gunda I. Georg, Zhijun Wu

Research output: Contribution to journalArticlepeer-review

34 Scopus citations

Abstract

(R)-(+)-1-(1-Naphthyl)ethylimines were found to be moderately better chiral templates in the Staudinger reaction in comparison to (R)-(+)-1-(phenyl)ethylimines. The best diastereoselectivities and yields were obtained with (R)-(+)-1-(1-naphthyl)ethylimines when toluene was used as the solvent. The resulting diastereomeric cis β-lactams were separated by silica gel flash column chromatography or recrystallization.

Original languageEnglish (US)
Pages (from-to)381-384
Number of pages4
JournalTetrahedron Letters
Volume35
Issue number3
DOIs
StatePublished - Jan 17 1994

Keywords

  • (R)-(+)-1-(1-naphthyl)ethylamine
  • (R)-(+)-1-(phenyl)ethylamine
  • Staudinger reaction
  • asymmetric synthesis
  • chiral template
  • solvent effects
  • β-lactams

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