SuFEx-Click Approach for the Synthesis of Soluble Polymer-Bound MacMillan Catalysts for the Asymmetric Diels–Alder Reaction

Novel polymeric MacMillan catalysts were prepared from modified chiral imidazolidin-4-one monomers via sulfur(VI) fluoride exchange chemistry. The resulting polysulfates containing chiral imidazolidin-4-one units could be employed as polymeric organocatalysts for the asymmetric Diels–Alder reaction....

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Bibliographic Details
Published inCatalysts Vol. 11; no. 9; p. 1044
Main Authors Lee, Woong-Sup, Li, Linzi, Kim, Byeong Moon
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 01.09.2021
Subjects
asymmetric catalysis
Asymmetry
Catalysis
Catalysts
Catalytic activity
Chemical reactions
Chemical synthesis
Design
Diels-Alder reactions
Enantiomers
Fluorides
MacMillan catalyst
Molecular weight
Polymerization
Polymers
recoverable organocatalyst
Selectivity
soluble polymer catalyst
sulfur(VI) fluoride exchange (SuFEx)
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Summary:Novel polymeric MacMillan catalysts were prepared from modified chiral imidazolidin-4-one monomers via sulfur(VI) fluoride exchange chemistry. The resulting polysulfates containing chiral imidazolidin-4-one units could be employed as polymeric organocatalysts for the asymmetric Diels–Alder reaction. With the use of these polysulfate catalysts, sufficient catalytic activity and enantioselectivity were obtained, which were similar to those obtained by monomeric catalysts in a homogeneous catalytic reaction. In addition, the polysulfate catalysts could be recovered and reused five times without a considerable loss of activity and selectivity.
ISSN:2073-4344
2073-4344
DOI:10.3390/catal11091044