Diethylzinc-mediated one-step stereoselective synthesis of alpha-fluoroacrylates from aldehydes and ketones. Two different pathways depending on the carbonyl partner.

A efficient methodology allowing the one-pot stereoselective synthesis of alpha-fluoroacrylates, based on the addition of ethyl dibromofluoroacetate to a carbonyl derivative using diethylzinc as organometallic mediator, is described. Two different pathways have been identified depending on the involved carbonyl partner. In the case of aldehydes, an E2-type mechanism has been identified, whereas ketones go through an E1cb-type mechanism.