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Iron(ii)-folded single-chain nanoparticles: a metalloenzyme mimicking sustainable catalyst for highly enantioselective sulfa-Michael addition in water

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Abstract

Metalloenzyme is a source of inspiration for chemists who attempt to create versatile synthetic catalysts for aqueous catalysis. Herein, we impart metalloenzyme-like characteristics to a chiral FeII–oxazoline complex by incorporating an Fe(II) ion into a chiral oxazoline-containing discrete self-folded polymer, to realize highly enantioselective sulfa-Michael addition (SMA) in water. Intrachain FeII–oxazoline complexation together with hydrophobic interactions triggers the self-folding of the oxazoline-containing single polymeric chain in water. The formed FeII-folded single-chain polymeric nanoparticles (SCPNs) significantly accelerate the aqueous asymmetric SMA reaction via a self-folded hydrophobic compartment around the catalytic sites, reminiscent of metalloenzymatic catalysis. In addition, they can be facilely recovered for reuse by simple thermo-controlled separation due to their thermo-responsive properties. Such metallo-folded SCPNs combine the benefits of transition metal- and bio-catalyst, and avoid the tedious procedures of separation, which is a benefit for energy-saving and industrial applications.

Graphical abstract: Iron(ii)-folded single-chain nanoparticles: a metalloenzyme mimicking sustainable catalyst for highly enantioselective sulfa-Michael addition in water

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Supplementary files

Article information


Submitted
17 Mar 2020
Accepted
07 Jun 2020
First published
19 Jun 2020

Green Chem., 2020, Advance Article
Article type
Paper

Iron(II)-folded single-chain nanoparticles: a metalloenzyme mimicking sustainable catalyst for highly enantioselective sulfa-Michael addition in water

W. Wang, J. Wang, S. Li, C. Li, R. Tan and D. Yin, Green Chem., 2020, Advance Article , DOI: 10.1039/D0GC00949K

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