Issue 36, 2005
From the journal:

Chemical Communications

Ammonium directed dihydroxylation of N,N-dibenzylaminocyclohex-2-ene: metal-free syntheses of the diastereoisomers of 3-dibenzylamino-1,2-dihydroxycyclohexane

Stephen G. Davies,*a   Marcus J. C. Longa  and  Andrew D. Smitha  

* Corresponding authors

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

Abstract

Treatment of N,N-dibenzylaminocyclohex-2-ene with mCPBA in the presence of CCl3CO2H gives 1,2-anti-2,3-syn-1-trichloroacetoxy-2-hydroxy-3-N,N-dibenzylaminocyclohexane with high diastereoselectivity; this methodology has been used to facilitate the metal-free stereoselective syntheses of all the diastereoisomers of 3-dibenzylamino-1,2-dihydroxycyclohexane.

Graphical abstract: Ammonium directed dihydroxylation of N,N-dibenzylaminocyclohex-2-ene: metal-free syntheses of the diastereoisomers of 3-dibenzylamino-1,2-dihydroxycyclohexane

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Article information

DOI
https://doi.org/10.1039/B509088A
Article type
Communication
Submitted
29 Jun 2005
Accepted
18 Jul 2005
First published
09 Aug 2005

Chem. Commun., 2005, 4536-4538

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Ammonium directed dihydroxylation of N,N-dibenzylaminocyclohex-2-ene: metal-free syntheses of the diastereoisomers of 3-dibenzylamino-1,2-dihydroxycyclohexane

S. G. Davies, M. J. C. Long and A. D. Smith, Chem. Commun., 2005, 4536 DOI: 10.1039/B509088A

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