Venugopal, Navyasree and Moser, Johannes and Vojtickova, Margareta and Cisarova, Ivana and Koenig, Burkhard and Jahn, Ullrich (2022) Single Electron Transfer-Induced Selective alpha-Oxygenation of Glycine Derivatives. ADVANCED SYNTHESIS & CATALYSIS, 364 (2). pp. 405-412. ISSN 1615-4150, 1615-4169
Full text not available from this repository. (Request a copy)Abstract
Modification of amino acids is an important strategy in organic and bioorganic chemistry. In contrast to common side-chain functionalization, backbone modification is much less explored. Especially glycine units seem to be attractive and versatile since a wide range of functionality can be potentially introduced. We report here oxidative modification of glycinates that are stable and enable further functionalization. Selective glycinate enolate oxidation by TEMPO or a FeCp2PF6/TEMPO reagent combination provides stable alkoxyamines in good to excellent yields. The methodology is expanded to glycine-containing dipeptides demonstrating selective oxygenation at the glycine unit. The orthogonal reactivity potential of oxygenated glycines for transformation to other amino acid derivatives is explored.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | FREE-RADICAL REACTIONS; AMINO-ACID; C-ALKYLATION; FOLDAMERS; PEPTIDES; RESIDUES; FUNCTIONALIZATION; DEPROTECTION; PALLADIUM; ENOLATE; Oxygenation; Glycine; Single electron oxidation; TEMPO; Alkoxyamines |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 25 Aug 2022 05:30 |
| Last Modified: | 25 Aug 2022 05:30 |
| URI: | https://pred.uni-regensburg.de/id/eprint/46935 |
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