5.05 The Paternò–Büchi Reaction

Abstract

The Paternò–Büchi reaction is a photochemical reaction between a carbonyl compound and an alkene to give the corresponding oxetane. In this chapter, the mechanism of the reaction is discussed. On this basis the described use in the reaction with electron rich alkenes (enol ethers, enol esters, enol silyl ethers, enamines, and heterocyclic compounds) has been reported. The stereochemical behavior of the reaction is particularly stressed. The authors have pointed out the reported application of this reaction to the synthesis of naturally occurring compounds.