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

Hammill, JT and Contreras-García, J and Virshup, AM and Beratan, DN and Yang, W and Wipf, P (2010) Synthesis and chemical diversity analysis of bicyclo[3.3.1]non-3-en-2-ones. Tetrahedron, 66 (31). 5852 - 5862. ISSN 0040-4020

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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.


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Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Hammill, JT
Contreras-García, J
Virshup, AM
Beratan, DN
Yang, W
Wipf, Ppwipf@pitt.eduPWIPF
Date: 31 July 2010
Date Type: Publication
Journal or Publication Title: Tetrahedron
Volume: 66
Number: 31
Page Range: 5852 - 5862
DOI or Unique Handle: 10.1016/j.tet.2010.04.112
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0040-4020
PubMed Central ID: PMC2925319
PubMed ID: 20798897
Date Deposited: 18 Jul 2014 21:17
Last Modified: 02 Feb 2019 15:56


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