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Issue 2, 2012
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Stereoselective piperidine synthesis through oxidative carbon–hydrogen bond functionalizations of enamides

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Abstract

N-Vinyl amides, carbamates, and sulfonamides that contain pendent π-nucleophiles react with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to form piperidine structures with good to excellent levels of efficiency and stereocontrol. Reactions proceed nearly instantaneously at room temperature. Transition state models show the preferred configuration around the intermediate acyliminium ion and the orientation of the nucleophile.

Graphical abstract: Stereoselective piperidine synthesis through oxidative carbon–hydrogen bond functionalizations of enamides

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Publication details

The article was received on 13 Sep 2011, accepted on 05 Oct 2011 and first published on 05 Oct 2011


Article type: Edge Article
DOI: 10.1039/C1SC00670C
Citation: Chem. Sci., 2012,3, 438-442
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    Stereoselective piperidine synthesis through oxidative carbon–hydrogen bond functionalizations of enamides

    G. J. Brizgys, H. H. Jung and P. E. Floreancig, Chem. Sci., 2012, 3, 438
    DOI: 10.1039/C1SC00670C

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