Abstract
A high-yielding enantioselective aqueous aldol reaction is carried out in the membrane of polymersome nanoreactors.
Highlights
L-Proline catalysts have been immobilised in the hydrophobic domain of a polymersome via a copper(I)-catalysed azide–alkyne cycloaddition (CuAAC) reaction
In a previous report[19] we demonstrated the embedding of a chiral copper bis(oxazoline) catalyst inside the hydrophobic domain of a polymersome membrane via a copper(I)-catalysed azide–alkyne cycloaddition (CuAAC) reaction.[20,21]
Given the powerful nature of L-proline in catalysing asymmetric aldol reactions, we envisioned that affixation of this organocatalyst in the membrane of a polymersome would yield a catalytic system that could mimic the activity of an aldolase enzyme.[22]
Summary
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. In the L-proline-catalysed asymmetric aldol reaction of 4-nitrobenzaldehyde with ketone donors, yields and selectivities significantly drop when water is added to the reaction mixture.[3] To overcome these incompatibility issues, the organocatalyst has to be effectively shielded from the aqueous environment.
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