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

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 s tereospecific giving up to three contiguous stereogenic centres and occurs efficiently irrespective of the stereochemistry.