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Issue 12, 2014
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Enantioselective synthesis of tetrahydroquinolines, tetrahydroquinoxalines, and tetrahydroisoquinolines via Pd-Catalyzed alkene carboamination reactions

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Abstract

A catalyst composed of Pd2(dba)3 and (S)-Siphos-PE provides excellent results in Pd-catalyzed alkene carboamination reactions between aniline derivatives bearing pendant alkenes and aryl or alkenyl halides. These transformations generate tetrahydroquinolines and tetrahydroquinoxalines that contain quaternary carbon stereocenters with high levels of asymmetric induction. In addition this catalyst also effects the asymmetric synthesis of tetrahydroisoquinolines via related transformations of 2-allylbenzylamines. In contrast to most other approaches to the asymmetric synthesis of these compounds, which frequently involve functional group interconversion or a single C–C or C–N bond-forming event, the carboamination reactions generate both a C–N bond, a C–C bond, and a stereocenter.

Graphical abstract: Enantioselective synthesis of tetrahydroquinolines, tetrahydroquinoxalines, and tetrahydroisoquinolines via Pd-Catalyzed alkene carboamination reactions

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The article was received on 07 May 2014, accepted on 12 Aug 2014 and first published on 27 Aug 2014


Article type: Edge Article
DOI: 10.1039/C4SC01327A
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Citation: Chem. Sci., 2014,5, 4840-4844
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    Enantioselective synthesis of tetrahydroquinolines, tetrahydroquinoxalines, and tetrahydroisoquinolines via Pd-Catalyzed alkene carboamination reactions

    B. A. Hopkins and J. P. Wolfe, Chem. Sci., 2014, 5, 4840
    DOI: 10.1039/C4SC01327A

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