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Molecules 2016, 21(11), 1493; doi:10.3390/molecules21111493

A Stereocontrolled Protocol to Highly Functionalized Fluorinated Scaffolds through a Fluoride Opening of Oxiranes

1
Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary
2
MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, Eötvös u. 6, H-6720 Szeged, Hungary
3
Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Valencia, Av. Vicente Andrés Estellés, s/n 46100 Valencia, Spain
*
Author to whom correspondence should be addressed.
Academic Editors: Bela Torok and Derek J. McPhee
Received: 31 August 2016 / Revised: 19 September 2016 / Accepted: 4 November 2016 / Published: 17 November 2016
(This article belongs to the Special Issue Fluorine Chemistry 2016)
View Full-Text   |   Download PDF [1093 KB, uploaded 17 November 2016]   |  

Abstract

A novel selective and substrate-dependent synthetic protocol has been developed towards the synthesis of various fluorine-containing, highly functionalized cycloalkane derivatives. The method involves the stereoselective epoxidation of some unsaturated cyclic β-amino acid derivatives as model compounds, followed by a regioselective fluoride opening of oxiranes under various conditions with Deoxofluor and XtalFluor-E reagents, thereby offering an insight into this new epoxide opening methodology with fluoride. View Full-Text
Keywords: oxirane; fluorination; amino acids; stereoselectivity; regioselectivity oxirane; fluorination; amino acids; stereoselectivity; regioselectivity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Remete, A.M.; Nonn, M.; Fustero, S.; Fülöp, F.; Kiss, L. A Stereocontrolled Protocol to Highly Functionalized Fluorinated Scaffolds through a Fluoride Opening of Oxiranes. Molecules 2016, 21, 1493.

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