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Issue 13, 2001
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The scope and limitation of the [1,4]-Sbenzyl participation and debenzylation in the stereochemically controlled synthesis of substituted thiolanes

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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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Publication details

The article was received on 26 Mar 2001, accepted on 17 May 2001 and first published on 13 Jun 2001


Article type: Paper
DOI: 10.1039/B102737A
Citation: J. Chem. Soc., Perkin Trans. 1, 2001,0, 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, 0, 1504
    DOI: 10.1039/B102737A

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