Radical cyclization of haloacetals:: The Ueno-Stork reaction

The formation of the C-C bond using radical cyclization of haloacetals (Ueno-Stork reaction) has proven to be an extremely efficient method to access gamma-lactones and related compounds. This reaction is also highly attractive for the regio- and stereoselective introduction of side chains to cyclic and acyclic allylic alcohols. It has been used as a key step in many natural product syntheses and has proven to be particularly efficient for the stereoselective generation of quaternary carbon centers. This review focuses on the different methods available to carry out this radical cyclization, as well as on the stereochemical aspect of the reaction and its applications in total synthesis.