Fischer, Theresa and Qui-Nhi Duong, and Mancheno, Olga Garcia (2017) Triazole-Based Anion-Binding Catalysis for the Enantioselective Dearomatization of N-Heteroarenes with Phosphorus Nucleophiles. [["eprint_typename_proceedings" not defined]]
Full text not available from this repository. (Request a copy)Abstract
The first enantioselective synthesis of chiral heterocyclic -amino phosphonates by nucleophilic dearomatization of quinolines and pyridines using an anion-binding organocatalysis approach is described. Chiral tetrakistriazoles were employed as efficient hydrogen-bond donor catalysts by forming a chiral close ion-pair with the in situ formed N-acyl salts and 2,2,2-trichlorethoxycarbonyl chloride (TrocCl). The ion-pair was subsequently treated with various phosphorus nucleophiles, such as silyl-protected dialkyl- and trialkylphosphites. Thus, the corresponding products were obtained in complete or high regioselectivities and up to 97:3 e.r. for quinolines or up to 89:11 e.r. for the more challenging pyridine substrates. This method allows for rapid access to substituted chiral cyclic -amino phosphonates, which can be easily transformed into phosphonic acid derivatives.
| Item Type: | ["eprint_typename_proceedings" not defined] |
|---|---|
| Uncontrolled Keywords: | ASYMMETRIC DEAROMATIZATION; AMINOPHOSPHONIC ACIDS; ALPHA-AMINOPHOSPHONATES; EFFICIENT SYNTHESIS; PHOSPHONATES; THIOUREA; ISOQUINOLINES; PYRIDINES; HYDROPHOSPHONYLATION; PHOSPHONYLATION; anion-binding; asymmetric catalysis; dearomatization; phosphorus nucleophiles; 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: | 14 Dec 2018 13:10 |
| Last Modified: | 11 Feb 2019 13:40 |
| URI: | https://pred.uni-regensburg.de/id/eprint/899 |
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