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    Accessing Stereochemically Rich Sultams via Microwave-Assisted, Continuous Flow Organic Synthesis (MACOS) Scale-out

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    Issue Date
    2011-08
    Author
    Organ, Michael G.
    Hanson, Paul R.
    Rolfe, Alan
    Samarakoon, Thiwanka Bandara
    Ullah, Farman
    Publisher
    Akadémiai Kiadó
    Type
    Article
    Article Version
    Scholarly/refereed, author accepted manuscript
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    Abstract
    The generation of stereochemically-rich benzothiaoxazepine-1,1′-dioxides for enrichment of high-throughput screening collections is reported. Utilizing a microwave-assisted, continuous flow organic synthesis platform (MACOS), scale-out of core benzothiaoxazepine-1,1′-dioxide scaffolds has been achieved on multi-gram scale using an epoxide opening/SNAr cyclization protocol. Diversification of these sultam scaffolds was attained via a microwave-assisted intermolecular SNAr reaction with a variety of amines. Overall, a facile, 2-step protocol generated a collection of benzothiaoxazepine-1,1′-dioxides possessing stereochemical complexity in rapid fashion, where all 8 stereoisomers were accessed from commercially available starting materials.
    URI
    http://hdl.handle.net/1808/23578
    DOI
    https://doi.org/10.1556/jfchem.2011.00008
    Collections
    • Chemistry Scholarly Works [586]
    Citation
    Organ, Michael G. et al. “Accessing Stereochemically Rich Sultams via Microwave-Assisted, Continuous Flow Organic Synthesis (MACOS) Scale-Out.” Journal of flow chemistry 1.1 (2011): 32–39. PMC. Web. 5 Apr. 2017.

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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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