eprintid: 22231
rev_number: 20
userid: 1419
dir: disk0/00/02/22/31
datestamp: 2014-07-18 21:17:45
lastmod: 2019-02-02 15:56:49
status_changed: 2014-07-18 21:17:45
type: article
metadata_visibility: show
item_issues_count: 0
eprint_status: archive
creators_name: Hammill, JT
creators_name: Contreras-García, J
creators_name: Virshup, AM
creators_name: Beratan, DN
creators_name: Yang, W
creators_name: Wipf, P
creators_email: 
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creators_email: pwipf@pitt.edu
creators_id: 
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creators_id: PWIPF
title: Synthesis and chemical diversity analysis of bicyclo[3.3.1]non-3-en-2-ones
ispublished: pub
divisions: sch_as_chemistry
full_text_status: public
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. © 2010 Elsevier Ltd.
date: 2010-07-31
date_type: published
publication: Tetrahedron
volume: 66
number: 31
pagerange: 5852 - 5862
refereed: TRUE
issn: 0040-4020
id_number: 10.1016/j.tet.2010.04.112
pmcid: PMC2925319
pmid: 20798897
citation:   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     
document_url: http://d-scholarship-dev.library.pitt.edu/22231/1/licence.txt