New expedient route to the stereoselective synthesis of fluorinated 1,3- diol derivatives via aluminum acetals derived from β-alkoxy esters and DIBAL

Article abstract of DOI:10.1016/S0040-4039(98)00879-X

On treating the aluminum acetal intermediates, generated in situ from ethyl 3-benzyloxy-2,2-difluoroalkanoates or 3-benzyloxy-4,4,4- trifluorobutanoate and diisobutylaluminum hydride at -78 °C for 1 h, with allylic stannanes in the presence of titanium(IV) dichloride diisopropoxide at 0 °C for 8 h or at -30 °C for 6 h, the corresponding allylated products, polyfluoro-1,3-diol derivatives, were obtained in good yields with high anti stereoselectivity.