Secondary and tertiary alcohols as nucleophiles in the stereospecific synthesis of substituted tetrahydrofurans by cyclisation of 1,3-diols with phenylsulfanyl migration

Article abstract of DOI:10.1016/0040-4039(96)00737-X

Rearrangement of a series of 4-phenylsulfanyl-1,3-diols with TsOH gives tetrahydrofurans stereospecifically and in high yield even if the nucleophile is a secondary or tertiary alcohol. We discuss the stereochemistry and acceptable substitution patterns of the diols which will carry out this reaction and define their limits.