Chelated [3,3]-rearrangements of difluoroallylic alcohols

✍ Scribed by M.J. Broadhurst; J.M. Percy; M.E. Prime

• Book ID: 104257668
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 216 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)01315-4

✦ Synopsis

Whereas the lithium enolates of acetate and propionate esters of difluoroallylic alcohols fragment rapidly, even at -78 °C, methoxy-and benzyloxy-acetates form chelated enolates which undergo smooth [3,3]-rearrangement as their silyl ketene acetals. The latent ketone function can be revealed under mild conditions (MeOH, SOC12) to afford very highly functionalised CF2 compounds.