Straightforward chemo- and stereoselective fluorocyclopropanation of allylic alcohols: exploiting the electrophilic nature of the not so elusive fluoroiodomethyllithium

Abstract

An unprecedented direct fluorocyclopropanation of allylic alcohols is reported. This simple method involves the not so elusive fluoroiodomethyllithium, a carbenoidic intermediate that under the developed conditions discloses its electrophilic nature. Gratifyingly, the reaction turned out to be highly chemo- and stereoselective, and DFT calculations provided insights into the structure and nature of this new type of carbenoid.