New reactions of functionalized β-lactams

Abstract

An easy synthesis of 4-(1- and 2-haloalkyl)azetidin-2-ones by a [2+2] cycloadditon protocol is described. Starting from these functionalized β-lactams, new pathways toward bicyclic β-lactams were developed via intramolecular nucleophilic substitutions and radical cyclizations. 4-(1- and 2-Haloalkyl)azetidin-2-ones also proved to be very useful starting products in the synthesis of various highly substituted aziridines, azetidines, and alkenoates. © 2005 IUPAC.