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    One-pot Synthesis of Lactams Using Domino Reactions: Combination of Schmidt Reaction with Sakuri and Aldol Reaction

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    Aubé_2009.pdf (1.386Mb)
    Issue Date
    2009-10-16
    Author
    Huh, Chan Woo
    Somal, Gagandeep K.
    Katz, Christopher E.
    Pei, Huanxing
    Zeng, Yibin
    Douglas, Justin T.
    Aubé, Jeffrey
    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 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://dx.doi.org/10.1021/jo901843w.
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    Abstract
    A series of domino reactions in which the intramolecular Schmidt reaction is combined with either a Sakurai reaction, an aldol reaction, or both is reported. The Sakurai reaction of an allylsilane with an azido-containing enone under Lewis acidic conditions followed by protonation of the resulting titanium enolate species allowed for a subsequent intramolecular Schmidt reaction. Alternatively, the intermediate titanium enolate could undergo an aldol reaction, followed by the intramolecular Schmidt reaction to form lactam products with multiple stereogenic centers. The stereochemical features of the titanium enolate aldol reaction with several 3-azidoaldehyde substrates during this domino process is discussed.
    URI
    http://hdl.handle.net/1808/23641
    DOI
    https://doi.org/10.1021/jo901843w
    Collections
    • Medicinal Chemistry Scholarly Works [244]
    Citation
    Huh, C. W., Somal, G. K., Katz, C. E., Pei, H., Zeng, Y., Douglas, J. T., & Aubé, J. (2009). One-pot Synthesis of Lactams Using Domino Reactions: Combination of Schmidt Reaction with Sakurai and Aldol Reactions. The Journal of Organic Chemistry, 74(20), 7618–7626. http://doi.org/10.1021/jo901843w

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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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