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Issue 3, 2013
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Effects of internal and external carboxylic acids on the reaction pathway of organocatalytic 1,4-addition reactions between aldehydes and nitroolefins

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Abstract

Kinetic and NMR spectroscopic studies revealed that the reaction pathway of conjugate addition reactions between aldehydes and nitroolefins depends on the presence or absence of a suitably positioned carboxylic acid group within the catalyst. The intermediate nitronate is trapped intramolecularly either by protonation (in the presence of a well positioned intramolecular carboxylic acid) or by C–C bond formation to a cyclobutane intermediate (in the absence of an intramolecular proton donor). These differences in the reaction pathway are reflected in different rate limiting steps of the reaction. The studies demonstrated that the preferred reaction pathway and thereby the rate limiting steps of the reaction can be influenced by additives of different acidity or the position of an intramolecular carboxylic acid group within the catalyst.

Graphical abstract: Effects of internal and external carboxylic acids on the reaction pathway of organocatalytic 1,4-addition reactions between aldehydes and nitroolefins

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Publication details

The article was received on 26 Oct 2012, accepted on 02 Jan 2013 and first published on 04 Jan 2013


Article type: Edge Article
DOI: 10.1039/C2SC21832A
Citation: Chem. Sci., 2013,4, 1312-1318
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    Effects of internal and external carboxylic acids on the reaction pathway of organocatalytic 1,4-addition reactions between aldehydes and nitroolefins

    J. Duschmalé, J. Wiest, M. Wiesner and H. Wennemers, Chem. Sci., 2013, 4, 1312
    DOI: 10.1039/C2SC21832A

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