The Journal of Organic Chemistry [SOPHY]

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.

 

Reference :

Maxime Hourtoule, Yongxiang Zheng, Anna Perfetto, Davide Luise, Ilaria Ciofini and Laurence Miesch

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

The Journal of Organic Chemistry, Publication Date (Web):March 28, 2022 : https://doi.org/10.1021/acs.joc.2c00302

Contact :

Laurence Miesch, équipe SOPhy, Institut de Chimie (UMR 7177).