Mechanistic investigations of a bifunctional squaramide organocatalyst in asymmetric Michael reaction and observation of stereoselective retroMichael reaction

Varga, Eszter and Mika, László Tamás and Csámpai, Antal and Holczbauer, Tamás and Kardos, György and Soós, Tibor (2015) Mechanistic investigations of a bifunctional squaramide organocatalyst in asymmetric Michael reaction and observation of stereoselective retroMichael reaction. RSC Advances (5). pp. 95079-95086. ISSN 2046-2069

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Abstract

The mechanism of the addition of acetylacetone to b-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 1 H-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

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