4.6 Article

A highly stereoselective and recyclable microgel-supported bifunctional sulfonamide organocatalyst for asymmetric alcoholysis of meso-cyclic anhydrides: a thermo-responsive organic nanoreactor

Journal

NEW JOURNAL OF CHEMISTRY
Volume 46, Issue 27, Pages 13269-13274

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2nj01914k

Keywords

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Funding

  1. National Natural Science Foundation of China [81172918, 51707122]
  2. Shanghai Municipal Education Commission [SLG14033]
  3. Open Project Program of Hubei Key Laboratory of Drug Synthesis [OPP2014ZD01]

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A novel thermosensitive bifunctional sulfonamide microgel catalyst, immobilized on a highly cross-linked three-dimensional network structure through covalent interactions, has been successfully used for catalyzing the asymmetric alcoholysis reaction with high yields and good stereoselectivity (up to 90% ee). Furthermore, the polymeric catalysts can be easily recovered and reused multiple times without apparent loss of catalytic activity and enantioselectivity.
A novel thermosensitive bifunctional sulfonamide microgel catalyst was synthesized by immobilization on a highly cross-linked three-dimensional network structure through covalent interactions. The microgel-supported organocatalyst has been successfully applied to catalyze the asymmetric alcoholysis reaction in high yields and good stereoselectivity (up to 90% ee). Furthermore, the polymeric catalysts could be recovered easily and reused multiple times (5 runs) without apparent loss of catalytic activity and enantioselectivity.

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