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.
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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.
- Staudinger reaction
- asymmetric synthesis
- α-hydroxy-β-amino acids