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

Journal Article (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.

Full Text

Duke Authors

Cited Authors

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

Published Date

  • March 2010

Published In

Volume / Issue

  • 66 / 31

Start / End Page

  • 5852 - 5862

PubMed ID

  • 20798897

Pubmed Central ID

  • PMC2925319

International Standard Serial Number (ISSN)

  • 0040-4020

Digital Object Identifier (DOI)

  • 10.1016/j.tet.2010.04.112


  • eng