Preparation of cyclic molecules bearing “strained” olefins using olefin metathesis

Recent advancements in metathesis catalyst design have allowed chemists to re-examine olefin metathesis as a route to systems bearing strained olefins embedded in their skeletons. Such ring systems include various azabicyclo [3.3.1] and [4.2.1] rings systems, the unique tricyclic ring system of the natural product ingenol, and strained macrocyclic systems exhibiting atropisomerism. Several examples of forming strained aromatic systems is also presented. The variety of different catalysts that have been developed allows for the possibility to select a catalyst having the necessary level of reactivity to access a strained system but also to avoid catalysts which may be so reactive as to favour ring-opening of the desired ring system.

Graphical abstractRecent advancements in metathesis catalyst design have allowed chemists to re-examine olefin metathesis as a route to systems bearing strained olefins embedded in their skeletons. The variety of different catalysts that has been developed allows for the possibility to select a catalyst having the necessary level of reactivity to access a strained system but also to avoid catalysts which may be so reactive as to favour ring-opening of the desired ring system.Figure optionsDownload full-size imageDownload as PowerPoint slide