Poly(styrene) resin-supported cobalt(III) salen cyclic oligomers as active heterogeneous HKR catalysts

A cross-linked poly(styrene) support functionalized with cobalt(III) salen cyclic oligomers that can be used as a catalyst for the hydrolytic kinetic resolution (HKR) of terminal epoxides is reported. This catalyst is the most active heterogeneous catalyst to date for the HKR of terminal epoxides and can be recycled more than six times with excellent enantioselectivities for the HKR of epichlorohydrin. A 3-fold rate enhancement was observed when conducting the HKR reaction with 6 equivalents of water compared to 0.6 equivalents. We hypothesize that this rate enhancement is due to water sequestration of the diol product from the organic phase, thereby maintaining a high local concentration of epoxides and catalyst in the organic phase.