Hydrolytic kinetic resolution of terminal epoxides catalyzed by fluorous chiral Co(salen) complexes

Cobalt complexes of fluorous chiral salen ligands have been synthesized and tested as catalysts in the hydrolytic kinetic resolution of terminal epoxides. Whereas the activity of heavily fluorinated complexes was found to be rather low, a ‘light fluorous’ complex was shown to be an efficient and highly selective catalyst for this asymmetric ring-opening reaction. Several strategies for the isolation of reaction products and the recovery of the fluorous catalyst are also discussed.