Chiral pyrrolidinium salts derived from menthol as precursor – synthesis and properties
| Autor: | Ewa Janus, Marcin Gano |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2017 |
| Předmět: |
Quantitative Biology::Biomolecules
010405 organic chemistry Chemistry General Chemical Engineering High Energy Physics::Lattice Industrial chemistry menthol General Chemistry 010402 general chemistry 01 natural sciences pyrrolidinium chiral salts chiral ionic liquids 0104 chemical sciences Condensed Matter::Soft Condensed Matter diels-alder reaction chemistry.chemical_compound Physics::Atomic and Molecular Clusters Organic chemistry Physics::Chemical Physics Menthol QD1-999 Biotechnology Diels–Alder reaction |
| Zdroj: | Polish Journal of Chemical Technology, Vol 19, Iss 3, Pp 92-98 (2017) |
| ISSN: | 1899-4741 |
| Popis: | Six new chiral pyrolidinium salts with chiral substituent at quaternary nitrogen atom were synthesized with high overall yields from (-)-menthol as cheap chiral precursor and were identified by NMR and HRMS spectroscopy. It was shown that anion type had the effect on chemical shift of protons adjacent to quaternary nitrogen atom and physical properties of these salts. Salts with NTf2 or NPf2 were in a liquid state at room temperature and characterized with the highest thermal stability among others. Furthermore, chiral ionic liquid with NTf2 anion was used as solvent in Diels-Alder reaction and gave higher yield and stereoselectivity than in ionic liquids with achiral cations. Synthesized chiral salts have the potential as chiral solvents in synthesis and auxiliaries in analytical methods to improve chiral recognition. |
| Databáze: | OpenAIRE |
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