Alginate- and <i>κ</i>-carrageenan-supported asymmetric organocatalysts: preparation, characterization, and catalytic activity for Friedel–Crafts alkylation

Alginate- and <i>κ</i>-carrageenan-supported imidazolidinone catalysts were newly prepared, and their catalytic activities for the Friedel-Crafts alkylation of 1-methylindole with crotonaldehyde were evaluated. The enantiomeric excess of the product was enhanced by using the polymer-supported catalysts consisting of an appropriate absolute configuration of imidazolidinones and alginate/<i>κ</i>-carrageenan <i>via</i> the cooperative effect that constructs a chiral environment more suited for asymmetric induction compared to imidazolidinone only. Further, the polymer-supported catalysts were easily removed from the reaction media by a simple filtration technique. <i>κ</i>-Carrageenan-supported catalysts were superior in terms of reusability compared to alginate-supported catalysts, likely due to the strong ionic interaction between the sulfate and ammonium moieties.

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Publication Details

Journal
RSC Advances
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ra05785j
Citations
2
Primary Topic
Seaweed-derived Bioactive Compounds
Type
article
Field-Weighted Citation Impact
4.55

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article

Alginate- and κ-carrageenan-supported asymmetric organocatalysts: preparation, characterization, and catalytic activity for Friedel–Crafts alkylation

Shogo Nakanishi, Fumio Sanda, Hiromitsu Sogawa, Manaho Murakishi
2 citations
RSC Advances
Seaweed-derived Bioactive Compounds
4.55
article

Alginate- and κ-carrageenan-supported asymmetric organocatalysts: preparation, characterization, and catalytic activity for Friedel–Crafts alkylation

Shogo Nakanishi, Fumio Sanda, Hiromitsu Sogawa, Manaho Murakishi
article en
2 citations

Abstract

Alginate- and <i>κ</i>-carrageenan-supported imidazolidinone catalysts were newly prepared, and their catalytic activities for the Friedel-Crafts alkylation of 1-methylindole with crotonaldehyde were evaluated. The enantiomeric excess of the product was enhanced by using the polymer-supported catalysts consisting of an appropriate absolute configuration of imidazolidinones and alginate/<i>κ</i>-carrageenan <i>via</i> the cooperative effect that constructs a chiral environment more suited for asymmetric induction compared to imidazolidinone only. Further, the polymer-supported catalysts were easily removed from the reaction media by a simple filtration technique. <i>κ</i>-Carrageenan-supported catalysts were superior in terms of reusability compared to alginate-supported catalysts, likely due to the strong ionic interaction between the sulfate and ammonium moieties.

RSC AdvancesVol. 15(37)
Kansai University (JP)
Hattori Hokokai Foundation, Kansai University, Iketani Science and Technology Foundation
Openalex Percentile: Top 6%
Seaweed-derived Bioactive Compounds
4.55
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Alginate- and <i>κ</i>-carrageenan-supported asymmetric organocatalysts: preparation, characterization, and catalytic activity for Friedel–Crafts alkylation — Shogo Nakanishi, Fumio Sanda, et al. · RSC Advances (2025) | TGRS Research Map | TGRS