[Journal cover design.67]Asymmetric Synthesis of Cyclobutanone via Lewis Acid Catalyzed Tandem Cyclopropanation/Semipinacol Rearrangement

Journal cover

A new method for the asymmetric formation of cyclobutanones has been developed using chiral Lewis acid catalysis. This method involves reacting α-silyloxyacroleins with α-alkyl or α-aryl diazoesters in the presence of a chiral oxazaborolidinium ion catalyst. The process yields various α-silyloxycyclobutanones with a chiral β-quaternary center in high yield (up to 91%) and excellent enantio- and diastereoselectivity (up to 98% ee and up to >20:1 dr). The synthetic potential of this method is highlighted by its ability to convert the product into various cyclic compounds such as γ-lactone, cyclobutanol, and cyclopentanone.-Journal cover design by scapiens

https://pubs.acs.org/doi/10.1021/jacs.8b06835

Share the Post:

Other Posts