Stereocontrolled synthesis of 1-oxacepham from 4-vinyloxyazetidin-2-one, a new building block

Article abstract of DOI:10.1016/S0957-4166(97)00310-8

A new methodology for 1-oxacepham synthesis is described. Readily available 4-vinyloxyazetidin-2-one 2 is shown to be a useful building block for β-lactam synthesis. N-Alkylation of 2 is followed by oxidation of the vinyloxy group to give 4-acyloxy-N-substituted azetidin-2-ones suitable for nucleophilic displacement at the C-4 carbon atom. The ring closure reaction offers high stereoselectivity.