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Employment of α-nitroketones in organic synthesis
Chandan Gharui1, Subhas Chandra Pan
1Department of Chemistry, Indian Institute of Technology Guwahati, 781039, India. span@iitg.ac.in.
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.
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