Surface Decoration of Cellulose With Trifluoromethylphenyl Substituted Thiourea: A Robust Hydrogen-Bonding Catalyst in Conjunction With L-Proline for the Asymmetric Direct Mannich Reaction

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dc.authorid0000-0003-3276-1413
dc.contributor.authorPoslu, Ayse Halic
dc.contributor.authorKoz, Gamze
dc.date.accessioned2026-02-08T15:14:45Z
dc.date.available2026-02-08T15:14:45Z
dc.date.issued2024
dc.departmentBursa Teknik Üniversitesi
dc.description.abstractCellulose is one of the most abundant biopolymers in nature. Despite being the subject of research in various fields, it is not as famous as chitosan in catalyst design. Herein, a novel thiourea-functionalized cellulose (CTU-6) was synthesized as a robust hydrogen bonding catalyst with the degree of substitution (DS) of 0.84. CTU-6 was characterized using Fourier transform infrared spectroscopy (FT-IR), scanning electron microscope (SEM), x-ray powder diffraction (XRD), proton nuclear magnetic resonance spectroscopy (1HNMR), solid-state cross-polarization magic angle spinning carbon-13 nuclear magnetic resonance (CP/MAS 13C-NMR), thermal gravimetric analysis (TGA) and elementel analysis. CTU-6 catalyzed the direct asymmetric Mannich reaction between acetone, aniline, and various aromatic aldehydes in cooperation with L-proline. The reaction exhibited excellent enantioselectivity, achieving up to 98% enantiomeric excess (ee) at room temperature. Incorporating trifluoromethylphenyl-substituted thiourea into the cellulose framework leverages its ability to form hydrogen bonds, thereby enabling precise control over the asymmetric induction. This study highlights the potential of cellulose-based catalysts in advancing asymmetric synthesis and their versatility in various organic reactions in cooperation with small chiral ligands. This synergy not only facilitates the efficient catalytic process but also improves the stereochemical outcomes of the reactions. This method underscores the importance of utilizing renewable and versatile cellulose materials in combination with chiral auxiliaries to achieve high levels of enantioselectivity.
dc.description.sponsorshipBursa Technical University Scientific Research Fund; [230D017]; [191N009]
dc.description.sponsorshipThe authors acknowledge the Bursa Technical University Scientific Research Fund for financial support (Grant numbers 230D017 and 191N009). The authors acknowledge that this paper is submitted in partial fulfillment of the requirements for the PhD degree at Bursa Technical University.
dc.identifier.doi10.1002/bip.23647
dc.identifier.issn0006-3525
dc.identifier.issn1097-0282
dc.identifier.issue1
dc.identifier.pmid39673235
dc.identifier.scopus2-s2.0-85211938979
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1002/bip.23647
dc.identifier.urihttps://hdl.handle.net/20.500.12885/5415
dc.identifier.volume116
dc.identifier.wosWOS:001380561900001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherWiley
dc.relation.ispartofBiopolymers
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzWOS_KA_20260207
dc.subjectasymmetric Mannich reaction
dc.subjectcellulose
dc.subjectL-proline
dc.subjectorganocatalysis
dc.subjectthiourea
dc.titleSurface Decoration of Cellulose With Trifluoromethylphenyl Substituted Thiourea: A Robust Hydrogen-Bonding Catalyst in Conjunction With L-Proline for the Asymmetric Direct Mannich Reaction
dc.typeArticle

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