Chimie

Preparation of Cyclobutene Acetals and Tricyclic Oxetanes through Photochemical Tandem and Cascade Reactions

Publié le - Angewandte Chemie

Auteurs : Julien Buendia, Zong Chang, Hendrik Eijsberg, Régis Guillot, Angelo Frongia, Francesco Secci, Juan Xie, Sylvie Robin, Thomas Boddaert, David Aitken

Abstract We describe a photochemical reaction using two starting materials, a cyclopent‐2‐enone and an alkene, which are transformed in a controlled manner via the initial [2+2]‐photocycloaddition adducts into cyclobutene aldehydes (conveniently trapped as stable acetals) or unprecedented angular tricyclic 4:4:4 oxetane‐containing skeletons. These compounds are formed through tandem or triple cascade photochemical reaction processes, respectively. Small libraries of each compound class were prepared, thus suggesting that this photochemistry approach opens new opportunities for synthesis design and for widening molecular diversity.