Ionic, Core-Corona Polymer Microsphere-Immobilized MacMillan Catalyst for Asymmetric Diels-Alder Reaction

The improvement of the catalytic activity of a heterogeneous chiral catalyst is one of the most critical issues, as are its recovery and reuse. The design of a heterogeneous chiral catalyst, including the immobilization method and the support polymer, is of significance for the catalytic activity in...

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Bibliographic Details
Published in:Catalysts 2019-11, Vol.9 (11), p.960
Main Authors: Ullah, Md. Wali, Haraguchi, Naoki
Format: Article
Language:English
Subjects:
Acids
Asymmetry
Catalysts
Catalytic activity
Chemical reactions
Chemical synthesis
Chloride
Cinnamaldehyde
Cyclopentadiene
Diels-Alder reactions
Enantiomers
Polymerization
Polymers
Recovery
Solvents
Sulfonic acid
Sulfur content
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Summary:The improvement of the catalytic activity of a heterogeneous chiral catalyst is one of the most critical issues, as are its recovery and reuse. The design of a heterogeneous chiral catalyst, including the immobilization method and the support polymer, is of significance for the catalytic activity in asymmetric reactions. An ionic, core-corona polymer microsphere-immobilized MacMillan catalyst (ICCC) was successfully synthesized by the neutralization reaction of sulfonic acid functionalized core-corona polymer microsphere (CCM–SO3H) with a chiral imidazolidinone precursor. We selected the core-corona polymer microsphere as the polymer support for the improvement of catalytic activity and recovery. The MacMillan catalyst was immobilized onto the pendant position of the corona with ionic bonding. ICCC exhibited excellent enantioselectivity up to 92% enantiomeric excess (ee) (exo) and >99% ee (endo) in the asymmetric Diels-Alder (DA) reaction of (E)-cinnamaldehyde and 1,3-cyclopentadiene. ICCC was quantitatively recovered by centrifugation because of the microsphere structure. The recovered ICCC was reused without significant loss of the enantioselectivity.
ISSN:2073-4344
2073-4344
DOI:10.3390/catal9110960