Issue 20, 2008
From the journal:

Organic & Biomolecular Chemistry

Ammonium-directed dihydroxylation: metal-free synthesis of the diastereoisomers of 3-aminocyclohexane-1,2-diol†

Caroline Aciro,a   Stephen G. Davies,*a   Paul M. Roberts,a   Angela J. Russell,ab   Andrew D. Smitha  and  James E. Thomsona  

* Corresponding authors

a Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, UK
E-mail: steve.davies@chem.ox.ac.uk

b Department of Pharmacology, University of Oxford, Mansfield Road, Oxford, UK

Abstract

The ammonium-directed, metal-free oxidation of 3-(N,N-dibenzylamino)cyclohex-1-ene with mCPBA in the presence of either trichloroacetic acid or tosic acid has been used as the key step to facilitate the synthesis of all the diastereoisomers of 3-aminocyclohexane-1,2-diol, in >98% de in each case.

Graphical abstract: Ammonium-directed dihydroxylation: metal-free synthesis of the diastereoisomers of 3-aminocyclohexane-1,2-diol

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Article information

DOI
https://doi.org/10.1039/B808812H
Article type
Paper
Submitted
27 May 2008
Accepted
29 Jul 2008
First published
20 Aug 2008

Org. Biomol. Chem., 2008,6, 3762-3770

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Ammonium-directed dihydroxylation: metal-free synthesis of the diastereoisomers of 3-aminocyclohexane-1,2-diol

C. Aciro, S. G. Davies, P. M. Roberts, A. J. Russell, A. D. Smith and J. E. Thomson, Org. Biomol. Chem., 2008, 6, 3762 DOI: 10.1039/B808812H

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