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Issue 36, 2014
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An easy access to α-aryl substituted γ-ketophosphonates: Lewis acid mediated reactions of 1,3-diketones with α-hydroxyphosphonates and tandem regioselective C–C bond cleavage

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Abstract

A range of α-aryl substituted γ-ketophosphonates is synthesised by Lewis acid mediated reactions of 1,3-diketones and easily accessible, inexpensive benzylic α-hydroxyphosphonates in an operationally simple method under solvent-free conditions without exclusion of air/moisture. A regioselective C–C bond cleavage for 1,3-diketones in a tandem fashion has also been demonstrated. Synthesis of a γ-ketophosphonate with phenol functionality at the α-position (structural analogue of raspberry ketone, a natural product) has also been presented.

Graphical abstract: An easy access to α-aryl substituted γ-ketophosphonates: Lewis acid mediated reactions of 1,3-diketones with α-hydroxyphosphonates and tandem regioselective C–C bond cleavage

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Publication details

The article was received on 28 May 2014, accepted on 22 Jul 2014 and first published on 23 Jul 2014


Article type: Paper
DOI: 10.1039/C4OB01091D
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2014,12, 7140-7149
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    An easy access to α-aryl substituted γ-ketophosphonates: Lewis acid mediated reactions of 1,3-diketones with α-hydroxyphosphonates and tandem regioselective C–C bond cleavage

    G. Pallikonda, M. Chakravarty and M. K. Sahoo, Org. Biomol. Chem., 2014, 12, 7140
    DOI: 10.1039/C4OB01091D

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