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Hussain, Yaseen ; R., Prasanna ; Empel, Claire ; Sharma, Deepak ; Kloene, Lennard ; Zhu, W. Felix ; Kaiser, Astrid ; Weizel, Lilia ; Proschak, Ewgenij ; Koenigs, Rene M. ; Chauhan, Pankaj:
A Photochemical Strategy towards Michael Addition Reactions of Cyclopropenes.
In: Angewandte Chemie International Edition.
Bd. 64
(2025)
.
- e202416956.
ISSN 1521-3773
DOI: https://doi.org/10.1002/anie.202416956
Abstract
The development of Michael addition reactions to conjugated cyclopropenes is a challenge in organic synthesis due to the fleeting and reactive nature of such strained Michael acceptor systems. Herein, the development of a photochemical approach towards such conjugated cyclopropenes is reported that serves as a strategic entry point to densely functionalized cyclopropanes in a diastereoselective fashion. The process involves the light-mediated generation of transient cyclopropenyl α,β-unsaturated esters from vinyl diazo esters, followed by an organic base catalyzed nucleophilic addition of N-heterocycles to directly access β-N-heterocyclic cyclopropanoic esters. With this synergistic approach, various trisubstituted cyclopropanes bearing N-heteroaryl and N-heterocyclic rings such as indole, pyrrole, benzimidazole, isatin, pyridinone, and quinolinone were accessed efficiently in good yield and decent to good diastereoselectivities. Further, β-indolyl cyclopropanoic acids have been synthesized and were successfully evaluated as FABP-4 inhibitors. Theoretical calculations have been performed to elucidate the mechanism, which was further supported by experimental findings.
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 07:30 |
| Letzte Änderung: | 28 Mär 2025 07:30 |
| URI: | https://eref.uni-bayreuth.de/id/eprint/93011 |