Synthesis and chemical diversity analysis of bicyclo[3.3.1]non-3-en-2-ones

publication · 11 years ago
by Jared T. Hammill, Aaron M. Virshup, David N. Beratan, Weitao Yang, Peter Wipf, Contreras-GarcĂ­a Julia (University of Pittsburgh)
Instant JChem
Functionalized bicyclo[3.3.1]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 identi!ed room temperature as well as microwave-mediated procedures, providing moderate to good yields (57e88%) 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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