Issue 27, 2005
From the journal:

Chemical Communications

Highly regioselective and diastereoselective epoxidation of allylic amines with Oxone†

Varinder K. Aggarwal*a  and  Guang Yu Fanga  

* Corresponding authors

a Department of Chemistry, University of Bristol, Cantock's Close, Bristol, UK
E-mail: V.Aggarwal@bristol.ac.uk
Fax: +44 (0)117 929 8611
Tel: +44 (0)117 9546319

Abstract

Allylic amines (as their protonated ammonium salts) can be epoxidised with high syn diastereoselectivity and regioselectivity at the proximal alkene in substrates with several double bonds using Oxone. The protonated ammonium cation activates the Oxone by hydrogen bonding, thus promoting the oxidation of groups within the vicinity of the complex.

Graphical abstract: Highly regioselective and diastereoselective epoxidation of allylic amines with Oxone

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Article information

DOI
https://doi.org/10.1039/B503516C
Article type
Communication
Submitted
10 Mar 2005
Accepted
04 May 2005
First published
09 Jun 2005

Chem. Commun., 2005, 3448-3450

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Highly regioselective and diastereoselective epoxidation of allylic amines with Oxone

V. K. Aggarwal and G. Yu Fang, Chem. Commun., 2005, 3448 DOI: 10.1039/B503516C

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