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    Reaction Pairing: A Diversity-Oriented Synthesis Strategy for the Synthesis of Diverse Benzofused Sultams

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    Issue Date
    2011-10-07
    Author
    Samarakoon, Thiwanka Bandara
    Loh, Joanna K.
    Rolfe, Alan
    Le, Lisa S.
    Yoon, Sun Young
    Lushington, Gerald H.
    Hanson, Paul R.
    Publisher
    American Chemical Society
    Type
    Article
    Article Version
    Scholarly/refereed, author accepted manuscript
    Rights
    This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/ol201962n.
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    Abstract
    A reaction pairing strategy centered on utilization of a reaction triad (sulfonylation, SNAr addition and Mitsunobu alkylation) generating skeletally diverse benzofused tricyclic and bicyclic sultams is reported. Pairing sulfonylation and SNAr reactions yields bridged, tricyclic and bicyclic benzofused sultams. Application of the Mitsunobu reaction in a sulfonylation–Mitsunobu–SNAr pairing allows access to benzo-oxathiazocine-1,1-dioxides, while a simple change in the order of pairing to sulfonylation–SNAr–Mitsunobu affords structurally different, benzofused bridged tricyclic sultams.
    URI
    http://hdl.handle.net/1808/23497
    DOI
    https://doi.org/10.1021/ol201962n
    Collections
    • Chemistry Scholarly Works [557]
    Citation
    Samarakoon, T. B., Loh, J. K., Rolfe, A., Le, L. S., Yoon, S. Y., Lushington, G. H., & Hanson, P. R. (2011). Reaction Pairing: A Diversity-Oriented Synthesis Strategy for the Synthesis of Diverse Benzofused Sultams. Organic Letters, 13(19), 5148–5151. http://doi.org/10.1021/ol201962n

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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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