Zwitterion‐Catalyzed Amino‐Dibromination of Nitroalkenes: Scope, Mechanism, and Application to The Synthesis of Glycinamides

Abstract

Glycinamides are valuable building blocks of natural products and biological relevant molecules. Many existing methods for the synthesis of glycinamides rely on harsh conditions. Herein, we report a zwitterion-catalyzed aminobromination of nitroalkenes using N-bromosuccinimide as the Br source and the amide donor. The resulting aminobromide products are converted into glycinamides.

Organobase-Catalyzed Umpolung of Amides: The Generation and Transfer of Carbamoyl Anion

“…To overcome the disadvantage, some newer approaches of amide synthesis were developed. For example, Yeung and coworkers have developed an efficient amino-dibromination of nitroalkenes for the synthesis of amide using zwitterion catalyst. In 2022, Johnson’s group reports a new amide synthetic method by the reaction of α-fuoronitroalkanes and N -aryl hydroxyl amines with a simple Brønsted base as the promoter.…”