One-Pot anti-Michael Regio- and Stereoselective Hydroamination of Activated N-Allenamides

Abstract

N-Allenamides, substituted by an ester at the γ-position, were obtained through addition of terminal ynamides with ethyl diazoacetate under copper catalysis for the first time. Regio- and stereoselective hydroamination of those activated N-allenamides provided exclusively E-configured captodative enamimes through a one-pot anti-Michael addition. Numerous ynamides as well as various secondary amines were adapted in this process.

Construction of C–N and C–O bonds based on N-allenamide functionalization

“…In the same year, our group (Miesch and coworkers) described a one-pot hydroamination reaction of ester-substituted N -allenamides at the γ-position 164 . 48 Activated N -allenamides 164 were obtained through the addition of ethyl diazoacetate 163 to terminal ynamides 162 under copper catalysis. These highly reactive activated species 164 underwent a regio- and stereoselective hydroamination with secondary amines to afford solely E -configuration enamines 165 .…”