relation: http://d-scholarship-dev.library.pitt.edu/22231/
title: Synthesis and chemical diversity analysis of bicyclo[3.3.1]non-3-en-2-ones
creator: Hammill, JT
creator: Contreras-García, J
creator: Virshup, AM
creator: Beratan, DN
creator: Yang, W
creator: Wipf, P
description: 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
type: Article
type: PeerReviewed
format: text/plain
language: en
rights: attached
identifier: http://d-scholarship-dev.library.pitt.edu/22231/1/licence.txt
identifier:   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     
relation: 10.1016/j.tet.2010.04.112