Chiral pyrrolidinium salts derived from menthol as precursor – synthesis and properties
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 adjace...
| Main Authors: | , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Sciendo
2017-09-01
|
| Series: | Polish Journal of Chemical Technology |
| Subjects: | |
| Online Access: | https://doi.org/10.1515/pjct-2017-0054 |
| _version_ | 1819115243049058304 |
|---|---|
| author | Janus Ewa Gano Marcin |
| author_facet | Janus Ewa Gano Marcin |
| author_sort | Janus Ewa |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-22T04:58:05Z |
| format | Article |
| id | doaj.art-06e83d27d0a34b9b9cbc0c0b3fac50aa |
| institution | Directory Open Access Journal |
| issn | 1899-4741 |
| language | English |
| last_indexed | 2024-12-22T04:58:05Z |
| publishDate | 2017-09-01 |
| publisher | Sciendo |
| record_format | Article |
| series | Polish Journal of Chemical Technology |
| spelling | doaj.art-06e83d27d0a34b9b9cbc0c0b3fac50aa2022-12-21T18:38:20ZengSciendoPolish Journal of Chemical Technology1899-47412017-09-01193929810.1515/pjct-2017-0054pjct-2017-0054Chiral pyrrolidinium salts derived from menthol as precursor – synthesis and propertiesJanus Ewa0Gano Marcin1West Pomeranian University of Technology, Szczecin, Faculty of Chemical Technology and Engineering, Department of Organic Chemical Technology, Pułaskiego 10, 70-322Szczecin, PolandWest Pomeranian University of Technology, Szczecin, Faculty of Chemical Technology and Engineering, Department of Organic Chemical Technology, Pułaskiego 10, 70-322Szczecin, PolandSix 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.https://doi.org/10.1515/pjct-2017-0054pyrrolidinium chiral saltschiral ionic liquidsmentholdiels-alder reaction |
| spellingShingle | Janus Ewa Gano Marcin Chiral pyrrolidinium salts derived from menthol as precursor – synthesis and properties Polish Journal of Chemical Technology pyrrolidinium chiral salts chiral ionic liquids menthol diels-alder reaction |
| title | Chiral pyrrolidinium salts derived from menthol as precursor – synthesis and properties |
| title_full | Chiral pyrrolidinium salts derived from menthol as precursor – synthesis and properties |
| title_fullStr | Chiral pyrrolidinium salts derived from menthol as precursor – synthesis and properties |
| title_full_unstemmed | Chiral pyrrolidinium salts derived from menthol as precursor – synthesis and properties |
| title_short | Chiral pyrrolidinium salts derived from menthol as precursor – synthesis and properties |
| title_sort | chiral pyrrolidinium salts derived from menthol as precursor synthesis and properties |
| topic | pyrrolidinium chiral salts chiral ionic liquids menthol diels-alder reaction |
| url | https://doi.org/10.1515/pjct-2017-0054 |
| work_keys_str_mv | AT janusewa chiralpyrrolidiniumsaltsderivedfrommentholasprecursorsynthesisandproperties AT ganomarcin chiralpyrrolidiniumsaltsderivedfrommentholasprecursorsynthesisandproperties |