Publications [#231927] of David N. Beratan

Journal Articles

  1. Hammill, JT; Contreras García, J; Virshup, AM; Beratan, DN; Yang, W; Wipf, P, "Synthesis and chemical diversity analysis of bicyclo[3.3.1]non-3-en-2-ones", Tetrahedron, 2010, 66(66), 5852-5862 [doi].
    (last updated on 2025/04/16)

    Abstract:
    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 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.