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Issue 20, 2002
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Stereochemically controlled synthesis of substituted 1,2-oxathianes

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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


Submitted
24 May 2002
Accepted
19 Aug 2002
First published
23 Sep 2002

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

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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