Selective Formal Transesterification of Fluorinated 2-(Trimethylsilyl)ethyl α-Imino Esters Mediated by TBAF

The scope of the transesterification reaction between β-fluorinated α-imino esters and various electrophiles in the presence of TBAF as fluorine source is described. The reaction is highly selective for alkyl iodides, bromides, and mesylates, while alkyl chlorides react at a significantly slower rate and tosylates do not react under the reaction conditions. This methodology represents a simple and useful alternative for the preparation of a wide variety of fluorinated α-imino esters.