A palladium-catalyzed ring-opening [3 + 2]-annulation of spirovinylcyclopropanyl oxindoles with seven-membered cyclic N-sulfonylimines has been developed. A wide range of seven-membered benzosultams featuring both a quaternary center and axially chiral… Click to show full abstract
A palladium-catalyzed ring-opening [3 + 2]-annulation of spirovinylcyclopropanyl oxindoles with seven-membered cyclic N-sulfonylimines has been developed. A wide range of seven-membered benzosultams featuring both a quaternary center and axially chiral biaryl scaffolds have been afforded in an average yield of 87% with moderate to excellent diastereoselectivities. The enantioenriched benzosultams were also accessed successfully in good yields with excellent atropoenantioselectivities enabled by the Pd2(dba)3/(S,S,S)-SKP ligand. The practical utility of this protocol was further demonstrated by the gram-scale reaction and diversified synthetic transformations of the desired seven-membered benzosultam.
Journal Title: Organic letters
Year Published: 2023
Link to full text (if available)
Share on Social Media: Sign Up to like & get
recommendations!