Regiospecific preparation and allylation of fluoromethyl ketone enol ethers via fluoro-olefination of 1,2,3-triol derivatives

✍ Scribed by Makoto Shimizu; Yuko Nakahara; Shigekazu Kanemoto; Hirosuke Yoshioka

• Publisher: Elsevier Science
• Year: 1987
• Tongue: French
• Weight: 257 KB
• Volume: 28
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)95392-9

✦ Synopsis

Fluoromethyl ketone enol ethers are regiospecifically prepared in good yields by treatment of 2-alkoxy-1,3-bis(t-butyldimethylsiloxy)alkane with TBAF-MsF, and subsequent thermal [ 3,3]-sigmatropic rearrangement on the 2-alkenyl enol ethers gives a-allylated products.

A fluoromethyl ketone bearing an a-branched alkenyl group has large potentials as the most convenient synthon for construction of mono-fluorinated mimics of bioactive natural compounds as prototype, in particular, of the isoprenoid unit structure. However, all the available