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

Publication at Faculty of Science, Central Library of Charles University |
2022

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 FeCp(2)PF(6)/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.