Synthesis of β‐Diamine Building Blocks by Photocatalytic Hydroamination of Enecarbamates with Amines, Ammonia and N−H Heterocycles

3‐Amino‐substituted saturated nitrogen heterocycles are an important subclass of β‐diamines, appearing in a number of clinical agents. Herein, we report a unified approach to these products based upon the regioselective photoredox‐mediated hydroamination of enecarbamates. The amine coupling partner...

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Veröffentlicht in:Chemistry : a European journal 2020-11, Vol.26 (65), p.14861-14865
Hauptverfasser: Francis, Daniel, Nelson, Adam, Marsden, Stephen P.
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Sprache:eng
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Zusammenfassung:3‐Amino‐substituted saturated nitrogen heterocycles are an important subclass of β‐diamines, appearing in a number of clinical agents. Herein, we report a unified approach to these products based upon the regioselective photoredox‐mediated hydroamination of enecarbamates. The amine coupling partner can encompass diverse amine types under a single set of reaction conditions, including primary alkyl amines, ammonia, aryl and heteroaryl amines, and N−H heterocycles. The method enables the synthesis of a wide range of pharmaceutically relevant building blocks. Medicinally important 3‐amino‐substituted cyclic amines can be accessed in a single step by photoredox‐catalysed hydroamination of cyclic enecarbamates. A diverse range of drug‐relevant amine substituents can be introduced under unified reaction conditions, including primary alkyl amines, ammonia, (hetero)aromatic amines, and N‐heterocycles (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202003562