Amino Acids as Catalysts for the Regioselective Rearrangement of Epoxides into Ketones

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 24, 2025

The combination of a natural amino acid (AA) (l-Glu, l-Tyr, and l-Lys) tetrabutylammonium iodide was efficiently employed as catalytic framework for the Meinwald rearrangement various epoxides into their respective ketones under microwave irradiation solvent-free conditions. designed system has shown good performance in conversion with different functional groups. reaction is regioselective toward ketone formation, these have been obtained to excellent yields. l-Glu found be most active AA this transformation. A mechanistic proposal, supported by computational simulations, also provided reinforce our experimental findings. suggested mechanism computing minimum energy path at density theory level through climbing-image nudged elastic band method. localized molecular orbital analysis based on intrinsic bond orbitals performed better understand role -TBAI along computed path. key both carboxylic moiety anion identified steps proposed mechanism, facilitating hydride transposition form final product.

Language: Английский

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Organic Catalysts and Ligands Derived from Amino Acids and Peptides

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134671 - 134671

Published: April 1, 2025

Language: Английский

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Biobased Derivatives From Olive Oil for Tuning Physically Crosslinked Poly(Vinyl Alcohol) Hydrogel Properties

Journal of Applied Polymer Science, Journal Year: 2025, Volume and Issue: unknown

Published: May 2, 2025

ABSTRACT This study presents the preparation and characterization of physically crosslinked polyvinyl alcohol (PVA)‐based hydrogels via freeze–thawing method, incorporating olive oil its derivatives, specifically epoxides diols. The derivatives were synthesized from using a mixture formic acid hydrogen peroxide as oxidants characterized through 1 H‐NMR FT‐IR spectroscopy. Hydrogels formulated by freezing 10 wt% PVA solutions containing varying concentrations (1 or 5 wt%) for 24 h, followed thawing at room temperature overnight. surface morphology, mechanical strength, thermal stability, antibacterial properties resulting systematically evaluated, influence chemical structure derivative on hydrogel was discussed supported molecular dynamics simulations.

Language: Английский

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Amino acids as eco-friendly bio-organocatalysts in ROCOP for the preparation of biobased oligomers from fatty acid epoxides and waste sunflower oil

Journal of Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 115903 - 115903

Published: Dec. 1, 2024

Language: Английский

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