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Issue 3, 2012
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Highly stereoselective catalytic conjugate addition of acyl anion equivalent to nitroolefins

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Abstract

Highly enantioselective conjugate addition of 2-unsubstituted azlactone 3 to various nitroolefins 4 was accomplished by the selective utilization of supramolecularly assembled, chiral tetraaminophosphonium aryloxide–arylhydroxide 1a·[2a]2 as a requisite catalyst. The key to this achievement is the polarity dependence of the molecular associations of type 1·[2]n and the crucial role of the proximal arylhydroxide 2 as a proton donor. The present method offers an attractive route to various optically active amino carbonyl compounds including β2-amino acids.

Graphical abstract: Highly stereoselective catalytic conjugate addition of acyl anion equivalent to nitroolefins

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Publication details

The article was received on 14 Sep 2011, accepted on 13 Nov 2011 and first published on 15 Nov 2011


Article type: Edge Article
DOI: 10.1039/C1SC00678A
Citation: Chem. Sci., 2012,3, 842-845
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    Highly stereoselective catalytic conjugate addition of acyl anion equivalent to nitroolefins

    D. Uraguchi, Y. Ueki and T. Ooi, Chem. Sci., 2012, 3, 842
    DOI: 10.1039/C1SC00678A

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