Chemoselective Synthesis of α-Fluoromethyl Amides via the Controlled Addition of LiCH 2 F to N-Aryl and N-Alkyl Isocyanates

Abstract

α-Fluoroacetamides were prepared through the nucleophilic addition of fluoromethyl-lithium to isocyanates. This single synthetic operation takes place under full chemocontrol and complete preservation of the stereochemical information. The protocol is flexible for both N-aryl and N-alkyl analogues, thus constituting a general technique for forming monofluoromethyl amides.