Solvent-Dependent Divergent Cyclization of Bicyclo[1.1.0]butanes

Zhang, Fuhao; Dutta, Subhabrata; Petti, Alessia; Rana, Debanjan; Daniliuc, Constantin G.; Glorius, Frank

Zusammenfassung

In this study, the solvent-dependent divergent 1,2- and 1,3-cyclization of bicyclo[1.1.0]butanes were achieved. This protocol straightforwardly led to a diverse range of oxa-bicyclic heptanes, which may serve as lead bioisosteres in drug discovery, as well as highly functionalized cyclobutanes with exceptional diastereoselectivity. Mechanistic investigation revealed that solvent effects dominate the reaction pathway, as the rate of acid-catalyzed isomerization of BCBs varies with different solvents. Furthermore, the gram-scale reactions and various post-synthetic modifications of the products demonstrated their potential applications in synthetic chemistry.