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

作者：Liu, Keyuan; Ye, Long; Wang, Yao; Du, Ganhong; Jiang, Liming^*

来源：Polymers, 2018, 10(9): 1004.

DOI：10.3390/polym10091004

• organocatalysis
• micelle
• poly(2-oxazoline)
• asymmetric aldol reaction
• pseudopeptide

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.

• 出版日期2018-9
• 单位浙江大学