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Polymers 2018, 10(9), 1004;

A Pseudopeptide Polymer Micelle Used for Asymmetric Catalysis of the Aldol Reaction in Water

MOE Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, China
Author to whom correspondence should be addressed.
Received: 12 August 2018 / Revised: 4 September 2018 / Accepted: 5 September 2018 / Published: 10 September 2018
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Micelles assembled from amphiphilic molecules have proved to be ideal scaffolds to construct artificial catalysts mimicking enzymatic catalytic behavior. In this paper, we describe the synthesis of amphiphilic poly(2-oxazoline) derivatives with l-prolinamide units in the side chain and their application in asymmetric aldol reactions. Upon dissolution in water, the pseudopeptide polymers self-assembled into particles with different sizes, relying on the copolymer composition and distribution of hydrophilic/hydrophobic segments in the polymer chain. A preliminary study has demonstrated that the catalytic activity of these polymeric organocatalysts are strongly dependent on the aggregated architecture. The micelle-type assemblies can act as nanoreactors to efficiently promote the direct aldolisation of cyclohexanone with aromatic aldehydes in aqueous media, affording anti-aldol products in excellent yields (88–99%) and higher stereoselectivities (90/10 dr, 86% ee) compared to their nonmicellar systems under identical conditions. View Full-Text
Keywords: organocatalysis; micelle; poly(2-oxazoline); asymmetric aldol reaction; pseudopeptide organocatalysis; micelle; poly(2-oxazoline); asymmetric aldol reaction; pseudopeptide

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Liu, K.; Ye, L.; Wang, Y.; Du, G.; Jiang, L. A Pseudopeptide Polymer Micelle Used for Asymmetric Catalysis of the Aldol Reaction in Water. Polymers 2018, 10, 1004.

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