Aqueous asymmetric aldol reactions in polymersome membranes

Abstract

l-Proline catalysts have been immobilised in the hydrophobic domain of a polymersome via a copper(i)-catalysed azide-alkyne cycloaddition (CuAAC) reaction. Utilisation of these nanoreactors in the asymmetric aldol reaction of cyclohexanone with 4-nitrobenzaldehyde afforded the corresponding β-hydroxyketones in quantitative yields and with excellent enantio- and diastereoselectivities. The polymersomes were recycled up to five times without any loss in activity or selectivity.