Issue 13, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

The scope and limitation of the [1,4]-Sbenzyl participation and debenzylation in the stereochemically controlled synthesis of substituted thiolanes

Jason Eames,*ab   Nikolai Kuhnertac  and  Stuart Warren*a  

* Corresponding authors

a University Chemical Laboratory, Lensfield Road, Cambridge, UK

b Department of Chemistry, Queen Mary, University of London, Mile End Road, London, UK

c Department of Chemistry, University of Surrey, Guildford, Surrey, UK

Abstract

Treatment of a series of 4-benzylsulfanyl-1,3-diols with toluene-p-sulfonyl chloride in pyridine gave substituted thiolanes in high yield by [1,4]-SBn participation and debenzylation with the chloride anion. The reaction is stereospecific giving up to three contiguous stereogenic centres and occurs efficiently irrespective of the stereochemistry.

Graphical abstract: The scope and limitation of the [1,4]-Sbenzyl participation and debenzylation in the stereochemically controlled synthesis of substituted thiolanes

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Article information

DOI
https://doi.org/10.1039/B102737A
Article type
Paper
Submitted
26 Mar 2001
Accepted
17 May 2001
First published
13 Jun 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 1504-1510

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The scope and limitation of the [1,4]-Sbenzyl participation and debenzylation in the stereochemically controlled synthesis of substituted thiolanes

J. Eames, N. Kuhnert and S. Warren, J. Chem. Soc., Perkin Trans. 1, 2001, 1504 DOI: 10.1039/B102737A

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