Issue 10, 2005
From the journal:

Organic & Biomolecular Chemistry

Deprotonation–electrophile trapping of terminal epoxides

David M. Hodgson,*a   Eirene H. M. Kirton,a   Steven M. Miles,a   Stéphanie L. M. Norsikian,a   Nigel J. Reynoldsa  and  Steven J. Cooteb  

* Corresponding authors

a Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, UK

b GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, UK

Abstract

Organolithium-induced deprotonation of terminal epoxides in the presence of appropriate diamine ligands allows trapping with a range of electrophiles, yielding functionalised di- and tri-substituted epoxides in good yields and with control of stereochemistry at the epoxide.

Graphical abstract: Deprotonation–electrophile trapping of terminal epoxides

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Article information

DOI
https://doi.org/10.1039/B502888D
Article type
Paper
Submitted
25 Feb 2005
Accepted
29 Mar 2005
First published
13 Apr 2005

Org. Biomol. Chem., 2005,3, 1893-1904

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Deprotonation–electrophile trapping of terminal epoxides

D. M. Hodgson, E. H. M. Kirton, S. M. Miles, S. L. M. Norsikian, N. J. Reynolds and S. J. Coote, Org. Biomol. Chem., 2005, 3, 1893 DOI: 10.1039/B502888D

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