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

Journal Article

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. © 2010 Elsevier Ltd.

Full Text

Duke Authors

Cited Authors

  • Hammill, JT; Contreras-García, J; Virshup, AM; Beratan, DN; Yang, W; Wipf, P

Published Date

  • 2010

Published In

Volume / Issue

  • 66 / 31

Start / End Page

  • 5852 - 5862

PubMed ID

  • 20798897

International Standard Serial Number (ISSN)

  • 0040-4020

Digital Object Identifier (DOI)

  • 10.1016/j.tet.2010.04.112