Single Electron Transfer-Induced Selective α-Oxygenation of Glycine Derivatives

0551919 - ÚOCHB 2023 RIV DE eng J - Journal Article
Venugopal, Navyasree - Moser, Johannes - Vojtíčková, Margaréta - Císařová, I. - König, B. - Jahn, Ullrich
Single Electron Transfer-Induced Selective α-Oxygenation of Glycine Derivatives.
Advanced Synthesis & Catalysis. Roč. 364, č. 2 (2022), s. 405-412. ISSN 1615-4150. E-ISSN 1615-4169
R&D Projects: GA MŠMT(CZ) EF16_019/0000729
Institutional support: RVO:61388963
Keywords : oxygenation * glycine * single electron oxidation * TEMPO * alkoxyamines
OECD category: Organic chemistry
Impact factor: 5.4, year: 2022
Method of publishing: Open access
https://doi.org/10.1002/adsc.202100964

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.
Permanent Link: http://hdl.handle.net/11104/0327120


Research data: CCDC