Stereospecific formation of tetrahydrofurans from substituted 2,8-Dioxabicyclo[3.2.1]oct-3-ylmethanols

Abstract

The reactions of some substituted 2,8-dioxabicyclo[3.2.1]oct-3-ylmethanols (hydroxy acetals) with oxalic acid in aqueous methanol solution gave tetrahydrofurans stereospecifically in good yields.The reactions occur with inversion of configuration at a tertiary carbon and are considered to proceed by a mechanism involving the carbonyl group generated by hydrolysis of the acetal function.