Issue 10, 2016

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
08 jun. 2016
Accepted
01 ago. 2016
First published
03 ago. 2016

Org. Chem. Front., 2016,3, 1295-1298

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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