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Updated: Jul 18, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
A Bioinspired Organocatalytic Cascade for the Selective Oxidation of Amines under Air
Martine Largeron1, Maurice-Bernard Fleury1
1UMR 8638 CNRS-Université Paris Descartes (Paris 5), Sorbonne Paris Cité, Faculté de Pharmacie de Paris, 4 avenue de l'Observatoire, 75270, Paris cedex 06, France.
Abstract:
A bioinspired organocatalytic cascade reaction for the selective aerobic oxidative cross-coupling of primary amines to imines is described. This approach takes advantages of commercially available pyrogallol monomeric precursor to deliver low loadings of natural purpurogallin in situ, under air. This is further engaged in a catalytic process with the amine substrate affording, under single turnover, the active biomimetic quinonoid organocatalyst and the homocoupled imine intermediate, which is then converted into cross-coupled imine after dynamic transimination. This organocatalytic cascade inspired by both purpurogallin biosynthesis and copper amine oxidases allows the aerobic oxidation of non-activated primary amines that non-enzymatic organocatalysts were not able to accomplish alone.
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