Lei, Tao and Graf, Sebastian and Schoell, Christopher and Kraetzschmar, Felix and Gregori, Bernhard and Appleson, Theresa and Breder, Alexander (2023) Asymmetric Photoaerobic Lactonization and Aza-Wacker Cyclization of Alkenes Enabled by Ternary Selenium-Sulfur Multicatalysis. ACS CATALYSIS, 13 (24). pp. 16240-16248. ISSN 2155-5435
Full text not available from this repository. (Request a copy)Abstract
An adaptable, sulfur-accelerated photoaerobic selenium-pi-acid ternary catalyst system for the enantioselective allylic redox functionalization of simple, nondirecting alkenes is reported. In contrast to related photoredox catalytic methods, which largely depend on olefinic substrates with heteroatomic directing groups to unfold high degrees of stereoinduction, the current protocol relies on chiral, spirocyclic selenium-pi-acids that covalently bind to the alkene moiety. The performance of this ternary catalytic method is demonstrated in the asymmetric, photoaerobic lactonization and cycloamination of enoic acids and unsaturated sulfonamides, respectively, leading to an averaged enantiomeric ratio (er) of 92:8. Notably, this protocol provides for the first time an asymmetric, catalytic entryway to pharmaceutically relevant 3-pyrroline motifs, which was used as a platform to access a 3,4-dihydroxyproline derivative in only seven steps with a 92:8 er.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ENANTIOSELECTIVE SYNTHESIS; PHOTOREDOX CATALYSIS; AMINO-ACID; ABSOLUTE-CONFIGURATION; PHOSPHORUS LIGANDS; DUAL-CATALYSIS; HECK REACTION; OXYGEN; ELECTROPHILES; ALKYLATION; enantioselectivity; photoredoxcatalysis; chiralselenium-pi-acids; alkenolides; 3-pyrrolines; 1,1 '-spirobiindane |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 27 Feb 2024 10:47 |
| Last Modified: | 27 Feb 2024 10:47 |
| URI: | https://pred.uni-regensburg.de/id/eprint/59100 |
Actions (login required)
 |
View Item |
