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Issue 30, 2017
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Enantioselective construction of quaternary tetrahydropyridines by palladium-catalyzed vinylborylation of alkenes

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Abstract

Here, the highly enantioselective construction of 3,3-disubstituted tetrahydropyridines via Pd(0)-catalyzed asymmetric vinylborylation of (Z)-1-iodo-dienes and B2pin2 in the presence of a (S)-p-CF3-BnPHOX ligand is reported. This process is supposed to be initiated by oxidative addition of Pd(0) to vinyl iodide, followed by transmetallation with B2pin2, insertion of the pendant alkene and reductive elimination of alkyl–Pd(II)-Bpin.

Graphical abstract: Enantioselective construction of quaternary tetrahydropyridines by palladium-catalyzed vinylborylation of alkenes

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Publication details

The article was received on 27 Feb 2017, accepted on 20 Mar 2017 and first published on 20 Mar 2017


Article type: Communication
DOI: 10.1039/C7CC01488K
Citation: Chem. Commun., 2017,53, 4270-4273
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    Enantioselective construction of quaternary tetrahydropyridines by palladium-catalyzed vinylborylation of alkenes

    Z. Jiang, L. Hou, C. Ni, J. Chen, D. Wang and X. Tong, Chem. Commun., 2017, 53, 4270
    DOI: 10.1039/C7CC01488K

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