Issue 26, 2014

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

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

Article information

Article type
Perspective
Submitted
22 Mar 2014
Accepted
16 Mai 2014
First published
23 Mai 2014

Org. Biomol. Chem., 2014,12, 4544-4549

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements