Abstract
The first application of (EO)n-(PO)m-(EO)n triblock copolymers as surfactants in asymmetric hydrogenation is described. We observed a dependence of the activity and enantioselectivity on the asymmetric hydrogenation of methyl (Z)-α-acetamidocinnamate on the length of the (PO)m domain of the copolymer. The activity and enantioselectivity were observed to be independent of the hydrophilic-lipophilic-balance (HLB) or the critical micelle concentration (cmc) of the copolymer. The size of the (EO)n unit does not play an important role, however the addition of a small amount of SDS enhances the enantioselectivities significantly. The triblock copolymers were also successfully used as phase transfer reagent in two-phase Suzuki carbon-carbon coupling reactions. The use of polymeric reagents in micellar and phase-transfer systems has the advantage that these reagents can be easily separated from the reaction mixture by means of a membrane.
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