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    1,3-Allylic Strain as a Strategic Diversification Element For Constructing Libraries of Substituted 2-Arylpiperidines

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    Coombs_AngewChemIntEdEngel_2011.pdf (1.027Mb)
    Issue Date
    2011-03-14
    Author
    Coombs, Thomas
    Lushington, Gerald H.
    Douglas, Justin T.
    Aubé, Jeffrey
    Publisher
    Wiley
    Type
    Article
    Article Version
    Scholarly/refereed, author accepted manuscript
    Rights
    Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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    Abstract
    Flipping diversity—Minimization of 1,3-allylic strain is a recurring element in the design of a stereochemically- and spatially-diverse collection of 2-arylpiperidines. Here, stereochemicallydiverse scaffolding is first constructed using A1,3 strain to guide the regioselective addition of nucleophiles, which serve as handles for further substitution. N-substitution with alkyl and acyl substituents again leverages A1,3 strain to direct each stereoisomer to two different conformer populations, doubling the number of library members
    URI
    http://hdl.handle.net/1808/23595
    DOI
    https://doi.org/10.1002/anie.201007133
    Collections
    • Chemistry Scholarly Works [520]
    Citation
    Coombs, T. C., Lushington, G. H., Douglas, J., & Aubé, J. (2011). 1,3-Allylic Strain as a Strategic Diversification Element For Constructing Libraries of Substituted 2-Arylpiperidines. Angewandte Chemie (International Ed. in English), 50(12), 2734–2737. http://doi.org/10.1002/anie.201007133

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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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