| Publications [#231927] of David N. Beratan
Journal Articles
- Hammill, JT; Contreras GarcĂa, 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, vol. 66 no. 66
(2010),
pp. 5852-5862, ISSN 0040-4020 [doi]
(last updated on 2024/04/23)
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.
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