Mancheno, Olga Garcia and Asmus, Soeren and Zurro, Mercedes and Fischer, Theresa (2015) Highly Enantioselective Nucleophilic Dearomatization of Pyridines by Anion-Binding Catalysis. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 54 (30). pp. 8823-8827. ISSN 1433-7851, 1521-3773
Full text not available from this repository. (Request a copy)Abstract
The asymmetric dearomatization of N-heterocycles is an important synthetic method to gain bioactive and synthetically valuable chiral heterocycles. However, the catalytic enantio- and regioselective dearomatization of the simplest six-membered-ring N-heteroarenes, the pyridines, is still very challenging. The first anion-binding-catalyzed, highly enantioselective nucleophilic dearomatization of pyridines with triazole-based H-bond donor catalysts is presented. Contrary to other more common NH-based H-bond donors, this type of organocatalyst shows a prominent higher C2-regioselectivity and is able to promote high enantioinductions via formation of a close chiral anion-pair complex with a preformed N-acyl pyridinium ionic intermediate. This method offers a straightforward and useful synthetic approach to chiral N-heterocycles from abundant and readily available pyridines.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ASYMMETRIC DEAROMATIZATION; HETEROAROMATIC-COMPOUNDS; LEWIS-BASE; SALTS; ORGANOCATALYSTS; DERIVATIVES; HYDROGENATION; CLEVIDIPINE; INVERSION; REAGENTS; anion-binding catalysis; dearomatization; enantioselectivity; pyridine; triazoles |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Olga Garcia Mancheño |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 05 Jul 2019 13:03 |
| Last Modified: | 05 Jul 2019 13:03 |
| URI: | https://pred.uni-regensburg.de/id/eprint/5194 |
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