The Prins Reaction: Advances and Applications

The acid-catalyzed alkene-aldehyde condensation, known as the Prins reaction, is reviewed. Lewis acids, organic acids and supported catalysts have been reported to assist both the Prins acyclic reaction and the Prins cyclization. Acetals and oxocarbenium ions (generated from aldehydes and alcohols) have been described as reacting systems in the Prins reaction. Prins cyclizations have been used to form mainly five- and six-membered rings, albeit formation of seven to nine rings have been described. The Prins reaction (and cyclization) has been developed as a key strategic element in the total synthesis of different natural products.