Issue 21, 2019

Employment of α-nitroketones in organic synthesis

Abstract

α-Nitroketones, useful bidentate reagents having nitro and keto functionalities, have been recently employed in a range of metal and organocatalytic domino reactions. In fact, several C–C, C–O, and C–N bond forming reactions were developed including Michael, domino-Michael, denitration, desymmetrisation, Mannich, nucleophilic addition/elimination and cycloaddition pathways. Unlike nitroalkanes, α-nitroketones can generate a range of active 1,3 dipolar intermediates such as nitronates and nitrile oxides which have been engaged in various cycloaddition reactions. Also α-functionalisation reactions such as arylations and halogenations were carried out. A variety of useful organic frameworks such as chromans, dihydrofurans, isoxazoles, pyrazoles etc. have been prepared. This review highlights the recent developments in the utilisation of α-nitroketones in organic synthesis and discusses the progress over the current years.

Graphical abstract: Employment of α-nitroketones in organic synthesis

Article information

Article type
Review Article
Submitted
10 Apr 2019
Accepted
25 Apr 2019
First published
26 Apr 2019

Org. Biomol. Chem., 2019,17, 5190-5211

Employment of α-nitroketones in organic synthesis

C. Gharui and S. C. Pan, Org. Biomol. Chem., 2019, 17, 5190 DOI: 10.1039/C9OB00828D

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