Recycling of a perfluoroalkylated BINOL ligand using fluorous solid-phase extraction

Abstract

After the asymmetric addition of allyltri-n-butyltin to benzaldehyde, a perfluoroalkylated BINOL-Sn complex was separated from the organic product using fluorous reverse phase silica gel. The lightly fluorinated ligand was then recovered by hydrolysis of the R_f6-BINOL-Sn complex with dilute hydrochloric acid and was reused three times without loss of activity or enantioselectivity.