Zurro, Mercedes and Asmus, Soeren and Beckendorf, Stephan and Mueck-Lichtenfeld, Christian and Mancheno, Olga Garcia (2014) Chiral Helical Oligotriazoles: New Class of Anion-Binding Catalysts for the Asymmetric Dearomatization of Electron-Deficient N-Heteroarenes. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 136 (40). pp. 13999-14002. ISSN 0002-7863,
Full text not available from this repository. (Request a copy)Abstract
Helical chirality and selective anion-binding processes are key strategies used in nature to promote highly enantioselective chemical reactions. Although enormous efforts have been made to develop simple helical chiral systems and thus open new possibilities in asymmetric catalysis and synthesis, the efficient use of synthetic oligo- and polymeric helical chiral catalysts is still very challenging and rather unusual. In this work, structural unique chiral oligotriazoles have been developed as C-H bond-based anion-binding catalysts for the asymmetric dearomatization of N-heteroarenes. These rotational flexible catalysts adopt a reinforced chiral helical conformation upon binding to a chloride anion, allowing high levels of chirality transfer via a close chiral anion-pair complex with a preformed ionic substrate. This methodology offers a straightforward and potent entry to the synthesis of chiral (bioactive)heterocycles with added synthetic value from simple and abundant heteroarenes.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | BOND DONORS; ENOL ETHERS; ORGANOCATALYSIS; ACTIVATION; LIGANDS; INVERSION; FOLDAMER; ACIDS; IONS; |
| 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: | 12 Aug 2019 08:06 |
| Last Modified: | 12 Aug 2019 08:06 |
| URI: | https://pred.uni-regensburg.de/id/eprint/9359 |
Actions (login required)
 |
View Item |
