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Silver- and Gold-Mediated Intramolecular Cyclization to Substituted Tetracyclic Isoquinolizinium Hexafluorostilbates

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    Silver- and Gold-Mediated Intramolecular Cyclization to Substituted Tetracyclic Isoquinolizinium Hexafluorostilbates
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    † State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China
    ‡ School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China
    [email protected]
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2010, 75, 17, 5810–5820
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    https://doi.org/10.1021/jo1006174
    Published August 4, 2010
    Copyright © 2010 American Chemical Society
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    Abstract

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    A convenient route for the synthesis of various charged tetracyclic isoquinolizinium hexafluorostilbates was developed using AgSbF6/AuCl(PPh3) for the intramolecular addition of amine to alkyne. The described process is tolerant of a variety of functional groups and broadens the diversity of substrates with the use of 8-substituted tetracyclic isoquinolizinium salts.

    Copyright © 2010 American Chemical Society

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    These authors contributed equally to this work.

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    Detailed experimental procedures, characterization data, copies of 1H and 13C NMR spectra for all products, and X-ray data for 2a (CIF). This material is available free of charge via the Internet at http://pubs.acs.org.

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2010, 75, 17, 5810–5820
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo1006174
    Published August 4, 2010
    Copyright © 2010 American Chemical Society
    Request reuse permissions

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