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Issue 14, 2011
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First asymmetric cascade reaction catalysed by chiral primary aminoalcohols

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Abstract

Readily available chiral primary 1,2-aminoalcohols and diamines have been explored as organocatalysts for a domino Michael–aldol reaction. Their application in this organocascade process afforded cyclohexanone A with high levels of reactivity (up to 91% yield) and stereoselectivity (>97 : 3 d.r., up to 93% ee). Depending on the acid cocatalyst different chiral species (cyclic secondary aminesvs. acyclic primary amines) might catalyse the process. In order to shed light on the catalytic activation, several experiments were carried out and a detailed possible reaction mechanism is proposed. Theoretical studies support the stereochemical outcome of the process.

Graphical abstract: First asymmetric cascade reaction catalysed by chiral primary aminoalcohols

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Publication details

The article was received on 14 Mar 2011, accepted on 11 Apr 2011 and first published on 12 Apr 2011


Article type: Paper
DOI: 10.1039/C1OB05400G
Citation: Org. Biomol. Chem., 2011,9, 5079-5085
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    First asymmetric cascade reaction catalysed by chiral primary aminoalcohols

    C. Arróniz, C. Escolano, F. J. Luque, J. Bosch and M. Amat, Org. Biomol. Chem., 2011, 9, 5079
    DOI: 10.1039/C1OB05400G

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