Catalytic stereoselective synthesis of cyclopentanones from donor-acceptor cyclopropanes and in situ -generated ketenes.
Shubhanjan MitraSophie M ConnollySaud AyidiMukulesh MondalManashi PandaBrian G KellyNessan J KerriganPublished in: Organic & biomolecular chemistry (2024)
A dual InBr 3 -EtAlCl 2 Lewis acidic system was found to be optimal for promoting the diastereoselective (3 + 2)-cycloaddition of donor-acceptor cyclopropanes with in situ -generated ketenes to form cyclopentanones. The desired products were formed in good to excellent yields (70-93% for 16 examples) and with good to excellent diastereoselectivity and enantiospecificity.