Galactose-Imines in the staudinger reaction

Gunda I. Georg, Eyüp Akgün, Peter M. Mashava, Mark Milstead, He Ping, Zhi jun Wu, David Vander Velde, Fusao Takusagawa

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33 Scopus citations

Abstract

Staudinger reaction of imines 1 and 2 derived from galactose with a variety of acid chlorides resulted in the formation of two β-lactams with cis configuration, typically in a 60:40 ratio and in good yields. The β-lactams were separated and the absolute stereochemistry of the diastereoisomers was determined by single crystal X-ray analysis and correlation of their 1H-NMR data.

Original languageEnglish (US)
Pages (from-to)2111-2114
Number of pages4
JournalTetrahedron Letters
Volume33
Issue number16
DOIs
StatePublished - Apr 14 1992

Bibliographical note

Funding Information:
Acknowledgements:F inanciala ssistancfer om theN ationalI nstituteso f Health (GM 42260a nd CA 52790), the Biomedical ResearchF und (RR 5606) at the University of Kansas, and the University of Zimbabwe ResearchB oardf or a travelg rantt o P. M. M. is acknowledged.

Keywords

  • Staudinger reaction
  • asymmetric synthesis
  • α-hydroxy-β-amino acids
  • β-lactams

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