Synthesis and chemical diversity analysis of bicyclo[3.3.1]non-3-en-2-ones |
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Authors: | Jared T Hammill Aaron M Virshup Weitao Yang Peter Wipf |
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Institution: | a Center for Chemical Methodologies and Library Development, University of Pittsburgh, Pittsburgh, PA 15260, USA b Department of Chemistry, Duke University, Durham, NC 27708, USA |
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Abstract: | Functionalized bicyclo3.3.1]non-3-en-2-ones are obtained from commercially available phenols by a hypervalent iodine oxidation, enone epoxidation, epoxide thiolysis, and intramolecular aldol reaction sequence. Reaction optimization studies identified room temperature as well as microwave-mediated procedures, providing moderate to good yields (57-88%) in the thiophenol-mediated epoxide opening and intramolecular aldol reaction. In addition, the isolation of a key intermediate and in situ NMR studies supported the mechanistic hypothesis. The bicyclic ring products occupy novel chemical space according to ChemGPS and Chemaxon chemical diversity and cheminformatics analyses. |
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Keywords: | Bicyclo[3 3 1]nonenones Chemical diversity analysis Ring-opening Epoxyketone rearrangement |
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