Aqueous asymmetric aldol reactions in polymersome membranes

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-hyd...

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Veröffentlicht in:Polymer chemistry 2015-01, Vol.6 (30), p.5358-5361
Hauptverfasser: van Oers, Matthijs C. M., Veldmate, Wouter S., van Hest, Jan C. M., Rutjes, Floris P. J. T.
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Sprache:eng
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Zusammenfassung: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.
ISSN:1759-9954
1759-9962
DOI:10.1039/C5PY00872G