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Issue 14, 2012
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Highly efficient asymmetric Michael addition of aldehyde to nitroolefin using perhydroindolic acid as a chiral organocatalyst

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Abstract

Perhydroindolic acids, the by-products obtained in the industrial production of a trandolapril intermediate, were used as chiral organocatalysts in asymmetric Michael addition reactions of aldehydes to nitroolefins. These proline-like catalysts are unique for their rigid bicyclic structure with two H atoms attached to the bridgehead C atoms lying on the opposite side of the ring. They therefore showed high efficiency in asymmetric Michael additions of aldehydes to nitroolefins. Under the optimal conditions, excellent diastereo- and enantioselectivities (up to 99/1 dr and 98% ee) were obtained with high chemical yields for a series of aldehydes and nitroolefins using only 5 mol% catalyst loading. The methodology features easily available catalysts, high catalytic efficiency and environmentally green procedures.

Graphical abstract: Highly efficient asymmetric Michael addition of aldehyde to nitroolefin using perhydroindolic acid as a chiral organocatalyst

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Publication details

The article was received on 01 Jan 2012, accepted on 02 Feb 2012 and first published on 07 Feb 2012


Article type: Paper
DOI: 10.1039/C2OB00003B
Citation: Org. Biomol. Chem., 2012,10, 2840-2846
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    Highly efficient asymmetric Michael addition of aldehyde to nitroolefin using perhydroindolic acid as a chiral organocatalyst

    L. Zhao, J. Shen, D. Liu, Y. Liu and W. Zhang, Org. Biomol. Chem., 2012, 10, 2840
    DOI: 10.1039/C2OB00003B

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