Diastereoselective Synthesis Of 2,6-Disubstituted 4-(Dimethoxymethyl)Tetra-Hydropyrans Using Tmsotf-Promoted Prins-Pinacol Cyclization

We have described a highly diastereoselective synthesis of 2,6-disubstituted 4-(dimethoxymethyl)tetrahydropyrans via TMSOTf-promoted Prins-pinacol reaction of methylene diol with acetals. This reaction provides an efficient procedure to synthesize functionalized tetrahydropyrans containing an acetal group at the C4 position with all-cis 2,4,6 relative configuration.