Issue 23, 2003
From the journal:

Organic & Biomolecular Chemistry

Enantioselective synthesis of epoxides by α-deprotonation—electrophile trapping of achiral epoxides

David M. Hodgson,*a   Timothy J. Buxton,a   Iain D. Cameron,a   Emmanuel Gras†a  and  Eirene H. M. Kirtona  

* Corresponding authors

a Dyson Perrins Laboratory, Department of Chemistry, University of Oxford, South Parks Road, Oxford, UK
E-mail: david.hodgson@chem.ox.ac.uk
Fax: +44(1865)275674

Abstract

Enantioselective α-deprotonation of achiral epoxides 1, 21, and 26 using organolithiums in the presence of (−)-sparteine 2 and subsequent electrophile trapping gives access to enantioenriched trisubstituted epoxides 9–17, 22, 23, 27 and 28 (in up to 86% ee).

Graphical abstract: Enantioselective synthesis of epoxides by α-deprotonation—electrophile trapping of achiral epoxides

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Article information

DOI
https://doi.org/10.1039/B309717J
Article type
Paper
Submitted
13 Aug 2003
Accepted
08 Oct 2003
First published
24 Oct 2003

Org. Biomol. Chem., 2003,1, 4293-4301

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Enantioselective synthesis of epoxides by α-deprotonation—electrophile trapping of achiral epoxides

D. M. Hodgson, T. J. Buxton, I. D. Cameron, E. Gras and E. H. M. Kirton, Org. Biomol. Chem., 2003, 1, 4293 DOI: 10.1039/B309717J

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