Organocatalytic asymmetric electrophilic tandem selenylation semipinacol rearrangement of 1-(1-arylvinyl)cyclobutanols†

Abstract

Chiral BINAM-derived sulfide and boron trifluoride etherate cocatalyzed enantioselective electrophilic selenylation/semipinacol rearrangement of 1-(1-arylvinyl)cyclobutanols was developed for the first time. Various selenium-containing cyclopentanones were obtained in moderate to excellent yields with good enantioselectivities. Moreover, a chiral quaternary carbon center was efficiently constructed via this reaction.