Mlostoń, Grzegorz; Wroblewska, Aneta; Heimgartner, Heinz (2016). Synthesis of optically active trifluoromethyl-substituted 2,3-dihydroimidazo[2,1-b]oxazoles. Journal of Fluorine Chemistry, 189:1-6.
The 2-unsubstituted imidazole N-oxides with a 3,3,3-trifluoro-2-hydroxypropyl group at N(1) in the presence of acetic anhydride undergo cyclization via the intramolecular nucleophilic attack of the hydroxyl group onto C(2) of the imidazole ring to give trifluoromethylated derivatives of 2,3-dihydroimidazo[2,1-b]oxazoles. This method, starting with enantiopure substrates, allows the preparation of enantiopure products in a one-pot procedure.
The 2-unsubstituted imidazole N-oxides with a 3,3,3-trifluoro-2-hydroxypropyl group at N(1) in the presence of acetic anhydride undergo cyclization via the intramolecular nucleophilic attack of the hydroxyl group onto C(2) of the imidazole ring to give trifluoromethylated derivatives of 2,3-dihydroimidazo[2,1-b]oxazoles. This method, starting with enantiopure substrates, allows the preparation of enantiopure products in a one-pot procedure.
| Item Type: | Journal Article, refereed, original work |
|---|---|
| Communities & Collections: | 07 Faculty of Science > Department of Chemistry |
| Dewey Decimal Classification: | 540 Chemistry |
| Scopus Subject Areas: | Life Sciences > Biochemistry
Physical Sciences > Environmental Chemistry Physical Sciences > Physical and Theoretical Chemistry Physical Sciences > Organic Chemistry Physical Sciences > Inorganic Chemistry |
| Language: | English |
| Date: | July 2016 |
| Deposited On: | 05 Aug 2016 09:18 |
| Last Modified: | 26 Jan 2022 09:46 |
| Publisher: | Elsevier |
| ISSN: | 0022-1139 |
| Funders: | National Science Center (Cracow) (Grants: OPUS-7 # UMO-2014/13/B/ST5/04004, and PRELUDIUM # UMO-2012/07/N/ST5/01873). |
| OA Status: | Green |
| Publisher DOI: | https://doi.org/10.1016/j.jfluchem.2016.07.014 |
Mlostoń, Grzegorz