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Issue 115, 2015
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Mechanistic investigations of a bifunctional squaramide organocatalyst in asymmetric Michael reaction and observation of stereoselective retro-Michael reaction

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Abstract

The mechanism of the addition of acetylacetone to β-nitrostyrene catalyzed by a cinchona based squaramide catalyst was studied in detail under synthetically relevant conditions. The reaction was monitored by in situ IR and 1H-NMR spectroscopy and a reaction mechanism was proposed based on these kinetics experiments. It was found that the reaction shows nearly first order dependence on both substrates and catalyst. Our investigations also revealed that the catalyst was able to promote stereoselective retro-Michael reaction.

Graphical abstract: Mechanistic investigations of a bifunctional squaramide organocatalyst in asymmetric Michael reaction and observation of stereoselective retro-Michael reaction

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Publication details

The article was received on 22 Sep 2015, accepted on 25 Oct 2015 and first published on 27 Oct 2015


Article type: Paper
DOI: 10.1039/C5RA19593D
Citation: RSC Adv., 2015,5, 95079-95086
  • Open access: Creative Commons BY-NC license
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    Mechanistic investigations of a bifunctional squaramide organocatalyst in asymmetric Michael reaction and observation of stereoselective retro-Michael reaction

    E. Varga, L. T. Mika, A. Csámpai, T. Holczbauer, G. Kardos and T. Soós, RSC Adv., 2015, 5, 95079
    DOI: 10.1039/C5RA19593D

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