Aqueous asymmetric aldol reactions in polymersome membranes

M.C.M. van Oers; W.S. Veldmate; J.C.M. van Hest; F.P.J.T. Rutjes

doi:10.1039/c5py00872g

Aqueous asymmetric aldol reactions in polymersome membranes

M.C.M. van Oers
, W.S. Veldmate
, J.C.M. van Hest
, F.P.J.T. Rutjes

Research output: Contribution to journal › Article › Academic › peer-review

22 Citations (Scopus)

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.

Original language	English
Pages (from-to)	5358-5361
Number of pages	4
Journal	Polymer Chemistry
Volume	6
Issue number	30
DOIs	https://doi.org/10.1039/c5py00872g
Publication status	Published - 14 Aug 2015
Externally published	Yes

Access to Document

10.1039/c5py00872g

Cite this

@article{9d7cc5ed88524404b0ed5a0907b188ae,

title = "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.",

author = "\{van Oers\}, M.C.M. and W.S. Veldmate and \{van Hest\}, J.C.M. and F.P.J.T. Rutjes",

year = "2015",

month = aug,

day = "14",

doi = "10.1039/c5py00872g",

language = "English",

volume = "6",

pages = "5358--5361",

journal = "Polymer Chemistry",

issn = "1759-9954",

publisher = "Royal Society of Chemistry",

number = "30",

}

TY - JOUR

T1 - Aqueous asymmetric aldol reactions in polymersome membranes

AU - van Oers, M.C.M.

AU - Veldmate, W.S.

AU - van Hest, J.C.M.

AU - Rutjes, F.P.J.T.

PY - 2015/8/14

Y1 - 2015/8/14

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/84937683416

U2 - 10.1039/c5py00872g

DO - 10.1039/c5py00872g

M3 - Article

AN - SCOPUS:84937683416

SN - 1759-9954

VL - 6

SP - 5358

EP - 5361

JO - Polymer Chemistry

JF - Polymer Chemistry

IS - 30

ER -

Aqueous asymmetric aldol reactions in polymersome membranes

Abstract

Access to Document

Other files and links

Fingerprint

Cite this