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  • The boron-mediated ketone-ketone aldol reaction

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    Author(s)
    Cergol, KM
    Turner, P
    Coster, MJ
    Griffith University Author(s)
    Coster, Mark J.
    Year published
    2005
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    Abstract
    The first examples of the directed, boron-mediated aldol reaction between different ketones are presented. Transformation of a variety of ketones to their corresponding boron enolates with Chx2BCl/Et3N, followed by reaction with acceptor ketones in diethyl ether, and oxidation of the resultant boron aldolate (H2O2, MeOH/pH 7 buffer), provided the aldol addition products. The reaction was most facile when cyclic ketones were used, with the highest yields obtained for the reaction of boron enolates with cyclohexanone as the acceptor.The first examples of the directed, boron-mediated aldol reaction between different ketones are presented. Transformation of a variety of ketones to their corresponding boron enolates with Chx2BCl/Et3N, followed by reaction with acceptor ketones in diethyl ether, and oxidation of the resultant boron aldolate (H2O2, MeOH/pH 7 buffer), provided the aldol addition products. The reaction was most facile when cyclic ketones were used, with the highest yields obtained for the reaction of boron enolates with cyclohexanone as the acceptor.
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    Journal Title
    Tetrahedron Letters
    Volume
    46
    Issue
    9
    Publisher URI
    http://www.elsevier.com/wps/find/journaldescription.cws_home/233/description#description
    DOI
    https://doi.org/10.1016/j.tetlet.2005.01.011
    Copyright Statement
    © 2005 Elsevier. This is the author-manuscript version of this paper. Reproduced in accordance with the copyright policy of the publisher. Please refer to the journal's website for access to the definitive, published version.
    Subject
    Medicinal and biomolecular chemistry
    Organic chemistry
    Publication URI
    http://hdl.handle.net/10072/16742
    Collection
    • Journal articles

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