Enantioselective Organocatalytic Syntheses and Ring‐Expansions of Cyclobutane Derivatives

Manuel Barday (1) , Pierre Bouillac (1) , Yoann Coquerel (1) , Muriel Amatore (1) , Thierry Constantieux (1) , Jean Rodriguez (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille

The progress in enantioselective organocatalysis have enabled efficient and highly stereoselective syntheses of cyclobutane derivatives, through (2 + 2) annulation reactions, overcoming the geometrical constraints inherent to these small cyclic molecules. More importantly, and taking advantage of their strain-releasing fragmentation, some cyclobutane derivatives, especially cyclobutanones and cyclobutenones, can now be regarded as versatile four-carbon atoms units amenable to the enantioselective construction of larger rings by (4 + n) annulation reactions to produce, five-, six-, seven-and eightmembered cyclic products. These recent developments concerning the enantioselective synthetic chemistry of cyclobutane derivatives under organocatalytic conditions are reviewed herein.

Mots clés: Medium-ring compounds; Organocatalysis; Ring expansion; Small ring systems; Strained molecules

Domaines: Chimie organique

Manuel Barday, Pierre Bouillac, Yoann Coquerel, Muriel Amatore, Thierry Constantieux, et al.. Enantioselective Organocatalytic Syntheses and Ring‐Expansions of Cyclobutane Derivatives. Illustration. France. 2021. ⟨hal-03370299⟩