Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2011 Apr 1;13(7):1832-5.
doi: 10.1021/ol103153f. Epub 2011 Mar 4.

Aqueous-phase deactivation and intramolecular [2 + 2 + 2] cycloaddition of oxanorbornadiene esters

Alexander A Kislukhin  1 , Cody J Higginson, M G Finn
Affiliations

Aqueous-phase deactivation and intramolecular [2 + 2 + 2] cycloaddition of oxanorbornadiene esters

Alexander A Kislukhin et al. Org Lett. .

Abstract

Both inter- and intramolecular degradation pathways were identified for the aqueous phase deactivation of oxanorbornadiene (OND) electrophiles, and propargylic OND esters were found to undergo facile intramolecular [2 + 2 + 2] homo-Diels-Alder cycloaddition in polar media.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Degradation pathways of OND electrophiles.
See this image and copyright information in PMC

References

    1. Cristina D, De Amici M, De Micheli C, Gandolfi R. Tetrahedron. 1981;37:1349–1357.
    1. Lautens M, Fillion E. J Org Chem. 1997;62:4418–4427. - PubMed
    1. Berkel SSv, Dirks AJ, Marjoke FD, Floris LvD, Jeroen JLMC, Roeland JMN, Floris PJTR. ChemBioChem. 2007;8:1504–1508. - PubMed
    1. Van Berkel SS, Dirks AJ, Silvie AM, Dennis LLP, Otto CB, Peter L, Floris LvD, Jeroen JLMC, Floris PJTR. ChemBioChem. 2008;9:1805–1815. - PubMed
    1. Laverman P, Meeuwissen SA, van Berkel SS, Oyen WJG, van Delft FL, Rutjes FPJT, Boerman OC. Nuclear Med Biol. 2009;36:749–757. - PubMed

Publication types