Efficient alkylsulfanyl (SMe, SEt and SCH2Ph) and sulfanyl (SH) migration in the stereospecific synthesis of substituted tetrahydrofurans

Article abstract of DOI:10.1016/0040-4039(96)00946-X

Treatment of a series of 4-RS-1,3-diols (R = Me, Et, Bn and H) with TsOH in CH₂Cl₂ gives substituted tetrahydrofurans. We discuss the scope of this reaction using structural variation of the migrating (RS) substituent. All reactions proceeded in high yield and give synthetically useful products.