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De Angelis, Luca ; Pei, Chao ; Narro, Ana L. ; Wherritt, Daniel ; Koenigs, Rene M. ; Doyle, Michael P.:
Polyfunctionalization of vicinal carbon centers and synthesis of unsymmetric 1,2,3,4-tetracarbonyl compounds.
In: Nature Communications.
Bd. 14
(2023)
.
- 1109.
ISSN 2041-1723
DOI: https://doi.org/10.1038/s41467-023-36757-w
Abstract
The synthesis and characterization of organic compounds with unusual atom or functional group connectivity is one of the main driving forces in the discovery of new synthetic methods that has raised the interest of chemists for many years. Polycarbonyl compounds are such compounds wherein multiple carbonyl groups are directly juxtaposed and influence each other’s chemical reactivity. While 1,2-dicarbonyl or 1,2,3-tricarbonyl compounds are well-known in organic chemistry, the 1,2,3,4-tetracarbonyl motif remains barely explored. Herein, we report on the synthesis of such 1,2,3,4-tetracarbonyl compounds employing a synthetic strategy that involves C-nitrosation of enoldiazoacetates, while the diazo functional group remains untouched. This strategy not only leverages the synthesis of 1,2,3,4-tetracarbonyl compounds to an unprecedented level, it also accomplishes the synthesis of 1,2,3,4-tetracarbonyl compounds, wherein each carbonyl group is orthogonally masked. Combined experimental and theoretical studies provide an understanding of the reaction mechanism and rationalize the formation of such 1,2,3,4-tetracarbonyl compounds.
Weitere Angaben
| Publikationsform: | Artikel in einer Zeitschrift |
|---|---|
| Begutachteter Beitrag: | Ja |
| Institutionen der Universität: | Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften > Fachgruppe Chemie |
| Titel an der UBT entstanden: | Nein |
| Themengebiete aus DDC: | 500 Naturwissenschaften und Mathematik > 540 Chemie |
| Eingestellt am: | 28 Mär 2025 10:23 |
| Letzte Änderung: | 28 Mär 2025 10:23 |
| URI: | https://eref.uni-bayreuth.de/id/eprint/93042 |