Synthesis of β-lactams from π-allyltricarbonyliron (lactone) complexes

Abstract

Several π-allyltricarbonyliron (lactone) complexes have been treated with an excess of benzylamine in the presence of Lewis acids to afford the corresponding lactam complexes by an S_N2′-like process. These lactam complexes were oxidised in good yield with ceric ammonium nitrate to provide a novel route to a variety of β-lactam compounds. Simple chemical transformations of the resulting β-lactams have been investigated; these include the conversion of the vinyl and isopropenyl side chains into hydroxyethyl substituents and the reductive removal of benzyl groups to afford the parent NH β-lactams.