The reduction of substituted 2,8-Dioxabicyclo[3,2,1]oct-3-ylmethyl methanesulfonates with lithium aluminium hydride

Abstract

2,8-Dioxabicyclo[3,2,1]oct-3-ylmethyl methanesulfonates undergo a two-step reduction with lithium aluminium hydride to yield tetrahydrofuran derivatives. The reduction of the carbon-oxygen bond of the acetal occurs with retention of configuration and the reaction then proceeds by reduction of an intermediate epoxide. The success of the reaction depends on the configuration of the methane-sulfonyloxy group.