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Enantioselective Construction of Quaternary Tetrahydropyridine by Palladium-Catalyzed Vinylborylation of Alkene

Abstract

The asymmetric synthesis of quaternary piperidine represents a substantial chemical research effort and would benefit natural product synthesis and medicinal chemistry. Herein, we describe the highly enantioselective construction of 3,3-disubstituted tetrahydropyridine via the Pd(0)-catalyzed asymmetric vinylborylation of (Z)-1-iodo-dienes and B2pin2 in the presence of (S)-p-CF3-BnPHOX ligand. 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.

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Publication details

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


Article type: Communication
DOI: 10.1039/C7CC01488K
Citation: Chem. Commun., 2017, Accepted Manuscript
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    Enantioselective Construction of Quaternary Tetrahydropyridine by Palladium-Catalyzed Vinylborylation of Alkene

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

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