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Borrmann, Ruediger ; Koenigs, Rene M. ; Zoller, Jochen ; Rueping, Magnus:
Asymmetric Hydrogenation of Cyclic Imines and Enamines: Access to 1,5-Benzodiazepine Pharmacophores.
In: Synthesis.
Bd. 49
(2017)
.
- S. 310-318.
ISSN 0039-7881
DOI: https://doi.org/10.1055/s-0036-1589401
Abstract
A new strategy towards the pharmacologically relevant class of dihydro-1,5-benzodiazepines was developed by applying a rhodium-catalyzed asymmetric hydrogenation. The approach represents an efficient protocol providing access to the optically active products in excellent yields (up to 99%) and with high enantioselectivities (up to 92% ee). The versatility of the methodology was demonstrated by a broad substrate scope including alkyl, aryl, and heteroaryl substituents as well as halides. Furthermore, investigations regarding the reaction mechanism were performed and unraveled a preferred reaction of the tautomeric enamine in the rhodium-catalyzed asymmetric hydrogenation.
Weitere Angaben
| Publikationsform: | Artikel in einer Zeitschrift |
|---|---|
| Begutachteter Beitrag: | Ja |
| Keywords: | asymmetric hydrogenation; rhodium catalysis; benzodiazepines; reduction; enamine |
| 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: | 03 Apr 2025 11:23 |
| Letzte Änderung: | 03 Apr 2025 11:23 |
| URI: | https://eref.uni-bayreuth.de/id/eprint/93203 |