The direct chemical conversion of peptides to β-lactams

Article abstract of DOI:10.1016/S0040-4020(01)92149-0

Appropriately protected seryldipeptides which have a relatively acidic proton (H¹ of 1) on the α' C can be efficiently converted to β-lactams by reaction with azodicarboxylates and triphenylphosphine. Application of the same reaction conditions to serylamides which lack an acidic α' proton provided dehydropeptides as the major product. Model reactions and potential intermediates which rationalize these results are described.