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ChemInform Abstract

β-Lactones can be converted to β-lactams in two steps via N-benzoylhydroxamic acid derivatives, obtained by treatment of the starting lactones with hydroxylamine (II) without or with minimal solvent (Et₂O), and subsequent intramolecular Mitsunobu reaction. This sequence proceeds with inversion of configuration. In the case of benzyloxy derivative (X), epimerization during the reaction leads to a decreased d.e. of product (XI). The reductive N—O bond cleavage is readily accomplished using SmI₂, in the case of derivative (X) without concomitant cleavage of the α-benzyloxy group.