Pecho, Franziska and Zou, You-Quan and Gramueller, Johannes and Mori, Tadashi and Huber, Stefan M. and Bauer, Andreas and Gschwind, Ruth M. and Bach, Thorsten (2020) A Thioxanthone Sensitizer with a Chiral Phosphoric Acid Binding Site: Properties and Applications in Visible Light-Mediated Cycloadditions. CHEMISTRY-A EUROPEAN JOURNAL, 26 (23). pp. 5190-5194. ISSN 0947-6539, 1521-3765
Full text not available from this repository. (Request a copy)Abstract
A chiral phosphoric acid with a 2,2'-binaphthol core was prepared that displays two thioxanthone moieties at the 3,3'-position as light-harvesting antennas. Despite its relatively low triplet energy, the phosphoric acid was found to be an efficient catalyst for the enantioselective intermolecular [2+2] photocycloaddition of beta-carboxyl-substituted cyclic enones (e.r. up to 93:7). Binding of the carboxylic acid to the sensitizer is suggested by NMR studies and by DFT calculations to occur by means of two hydrogen bonds. The binding event not only enables an enantioface differentiation but also modulates the triplet energy of the substrates.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | 2+2 PHOTOCYCLOADDITION REACTIONS; BRONSTED ACID; ASYMMETRIC INDUCTION; CARBOXYLIC-ACIDS; CYCLIC ENONES; PHOSPHORESCENCE; CATALYSIS; DERIVATIVES; ACTIVATION; ALPHA,BETA-ENONES; enantioselectivity; hydrogen bonds; organocatalysis; photochemistry; sensitizers |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Ruth Gschwind |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 26 Mar 2021 11:32 |
| Last Modified: | 26 Mar 2021 11:32 |
| URI: | https://pred.uni-regensburg.de/id/eprint/44742 |
Actions (login required)
 |
View Item |
