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

✍ Scribed by Takashi Ishihara; Atsuya Takahashi; Hidetoshi Hayashi; Hiroki Yamanaka; Toshio Kubota

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 228 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)00879-x

✦ Synopsis

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 qC 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 allvlated products, polyfluoro-1,3-diol derivatives, were obtained in good yields with high ant/stereoselectivity.