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

Eszter Varga, László Tamás Mika, Antal Csámpai, Tamás Holczbauer, György Kardos, Tibor Soós

Research output: Contribution to journalArticle

15 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)95079-95086
Number of pages8
JournalRSC Advances
Volume5
Issue number115
DOIs
Publication statusPublished - 2015

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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