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    Metal-Templated Assembly of Cyclopropane-Fused Diazepanones and Diazecanones via exo-trig Nucleophilic Cyclization of Cyclopropenes with Tethered Carbamates

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    Issue Date
    2018-10-24
    Author
    Maslivetc, Vladimir A.
    Frolova, Liliya V.
    Rogelj, Snezna
    Maslivetc, Anna A.
    Rubina, Marina
    Rubin, Michael
    Publisher
    American Chemical Society
    Type
    Article
    Article Version
    Scholarly/refereed, author accepted manuscript
    Rights
    Copyright © 2018 American Chemical Society
    Metadata
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    Abstract
    A strain-release-driven, cation-templated nucleophilic 7- and 8-exo-trig-cyclization of tethered Boc-protected amines to cyclopropenes is described. The featured reaction proceeds in diastereo- and regioselective fashion and allows for preparation of the corresponding 2,5-diazabicyclo[5.1.0]octan-6-ones and 2,6-diazabicyclo[6.1.0]nonan-7-ones as sole products in high yields. Preliminary studies on anticancer activities of these novel cyclopropane-fused medium heterocycles were performed.
    Description
    This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://doi.org/10.1021/acs.joc.8b02062.
    URI
    http://hdl.handle.net/1808/29735
    DOI
    https://doi.org/10.1021/acs.joc.8b02062
    Collections
    • Chemistry Scholarly Works [610]
    Citation
    Maslivetc, V. A., Frolova, L. V., Rogelj, S., Maslivetc, A. A., Rubina, M., & Rubin, M. (2018). Metal-Templated Assembly of Cyclopropane-Fused Diazepanones and Diazecanones via exo- trig Nucleophilic Cyclization of Cyclopropenes with Tethered Carbamates. The Journal of organic chemistry, 83(22), 13743–13753. doi:10.1021/acs.joc.8b02062

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    KU Libraries
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    785-864-8983

    KU Libraries
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    Lawrence, KS 66045
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    Contact KU ScholarWorks
    785-864-8983
    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    785-864-8983

    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    Image Credits
     

     

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