Chiral Trifluoromethylated Enamides: Synthesis and Applicability

Abstract

Enamides are valuable building blocks in organic synthesis that give access to complex nitrogen-containing compounds. However, despite their high interest, synthetic strategies to access enamides with carbon-centered chirality are scarce. Herein, we report a mild and robust synthetic method towards novel gamma-chiral, trifluoromethylated enamides from easily accessible alpha-chiral allylic amines through efficient chirality transfer (up to 99.5%) with excellent yields, diastereo- and enantioselectivities. A broad and diverse scope is presented that tolerates various substituents and functional groups. Additionally, multiple organic transformations were performed to access new chiral complex scaffolds. Among them, a novel protocol for the E/Z isomerization of enamides is presented.