Chelated [3,3]-rearrangements of difluoroallylic alcohols

Article abstract of DOI:10.1016/S0040-4039(97)01315-4

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 CMeOH,SOCl₂) to afford very highly functionalised CF₂ compounds.