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Issue 26, 2014
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Hydrogen bond directed epoxidation: diastereoselective olefinic oxidation of allylic alcohols and amines

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Abstract

This article compares the diastereoselective epoxidation of acyclic and cyclic allylic alcohols, with the chemo- and diastereoselective olefinic oxidation of a range of acyclic and cyclic allylic amines. The diastereoselectivity in these systems is compared and a discussion about the origin of this high diastereocontrol is also presented. The ammonium directed epoxidation methodology has been extended to more complex substrates and representative applications of this protocol in natural product synthesis are also summarised.

Graphical abstract: Hydrogen bond directed epoxidation: diastereoselective olefinic oxidation of allylic alcohols and amines

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Publication details

The article was received on 22 Mar 2014, accepted on 16 May 2014 and first published on 23 May 2014


Article type: Perspective
DOI: 10.1039/C4OB00616J
Citation: Org. Biomol. Chem., 2014,12, 4544-4549
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    Hydrogen bond directed epoxidation: diastereoselective olefinic oxidation of allylic alcohols and amines

    S. G. Davies, A. M. Fletcher and J. E. Thomson, Org. Biomol. Chem., 2014, 12, 4544
    DOI: 10.1039/C4OB00616J

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