Issue 20, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Stereochemically controlled synthesis of substituted 1,2-oxathianes

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-sulfanyl-1,3-diols with toluene-p-sulfonyl chloride and triethylamine in dichloromethane gives substituted 1,2-oxathianes as single diastereoisomers in high yield by cyclisation with formation of a S–O bond. The cyclisation occurs efficiently and the fate of each stereogenic centre (four in all) of the newly formed oxathiane ring is investigated.

Graphical abstract: Stereochemically controlled synthesis of substituted 1,2-oxathianes

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Article information

DOI
https://doi.org/10.1039/B205060A
Article type
Paper
Submitted
24 May 2002
Accepted
19 Aug 2002
First published
23 Sep 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 2282-2287

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Stereochemically controlled synthesis of substituted 1,2-oxathianes

J. Eames, N. Kuhnert and S. Warren, J. Chem. Soc., Perkin Trans. 1, 2002, 2282 DOI: 10.1039/B205060A

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