Photocatalytic Isomerization of (E)-Anethole to (Z)-Anethole
Korff, Marvin; Paulisch, Tiffany O.; Glorius, Frank; Doltsinis, Nikos L.; Wuensch, Bernhard
Research article (journal) | Peer reviewedAbstract
Natural product (E)-anethole was isomerized to (Z)-anethole in a photocatalytic reaction. For this purpose, a self-designed cheap photoreactor was constructed. Among 11 photosensitizers (organo and metal complex compounds), Ir(p-tBu-ppy)3 led to the highest conversion. Triplet energies of (E)- and (Z)-anethole were predicted theoretically by DFT calculations to support the selection of appropriate photosensitizers. A catalyst loading of 0.1 mol% gave up to 90% conversion in gram scale. Further additives were not required and mild irradiation with light of 400 nm overnight was sufficient. As a proof of concept, (E)- and (Z)-anethole were dihydroxylated diastereoselectively to obtain diastereomerically pure like- and unlike-configured diols, respectively.
Details about the publication
Authors from the University of Münster
| Doltsinis, Nikos | Professorship of solid state theory (Prof. Doltsinis) Center for Multiscale Theory and Computation (CMTC) |
| Glorius, Frank | Professur für Organische Chemie (Prof. Glorius) |
| Korff, Marvin | Professur für Pharmazeutische Chemie (Prof. Wünsch) |
| Paulisch, Tiffany | Professur für Organische Chemie (Prof. Glorius) |
| Wünsch, Bernhard | Professur für Pharmazeutische Chemie (Prof. Wünsch) |
Projects the publication originates from
RTG 2515: Chemical Biology of Ion Channels (Chembion) Duration: 01/10/2019 - 31/03/2024 | 1st Funding period Funded by: DFG - Research Training Group Type of project: Main DFG-project hosted at University of Münster |