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Issue 10, 2016
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Fe-Catalyzed reductive NO-bond cleavage – a route to the diastereoselective 1,4-aminohydroxylation of 1,3-dienes

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Abstract

The low-valent Fe-complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the reductive cleavage of N–O-bonds in oxazines under salt-free conditions using malononitrile as reductant. The mild reduction conditions allow the development of a sequence of [4 + 2]-cycloaddition/reductive cleavage, a process that can be considered as an efficient way for the diastereoselective 1,4-aminohydroxylation of 1,3-dienes.

Graphical abstract: Fe-Catalyzed reductive NO-bond cleavage – a route to the diastereoselective 1,4-aminohydroxylation of 1,3-dienes

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Publication details

The article was received on 08 Jun 2016, accepted on 01 Aug 2016 and first published on 03 Aug 2016


Article type: Research Article
DOI: 10.1039/C6QO00255B
Citation: Org. Chem. Front., 2016,3, 1295-1298
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    Fe-Catalyzed reductive NO-bond cleavage – a route to the diastereoselective 1,4-aminohydroxylation of 1,3-dienes

    S. Scholz and B. Plietker, Org. Chem. Front., 2016, 3, 1295
    DOI: 10.1039/C6QO00255B

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