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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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Article information


Submitted
13 Sep 2011
Accepted
05 Oct 2011
First published
05 Oct 2011

Chem. Sci., 2012,3, 438-442
Article type
Edge Article

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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