Zinc-Catalyzed Hydrocyanation of Ynamides and Photoisomerization, a General and Selective Access to E and Z Trisubstituted α-Enamidonitriles

The fully regio- and stereoselective Zn-catalyzed hydrocyanation of ynamides is reported and represents a general access to various trisubstituted E-alpha-enamidonitriles. The catalyst-free photoisomerization selectively yields the energetically comparable Z-stereoisomer. Finally, the synthetic potential of these new alpha-enamidonitriles was evaluated through the synthesis of original heterocycles.

Automated summary

The research reports a fully selective Zn-catalyzed hydrocyanation of ynamides, allowing the synthesis of various trisubstituted E-alpha-enamidonitriles. The catalyst-free photoisomerization results in the energetically comparable Z-stereoisomer. Furthermore, the synthetic potential of these newly synthesized alpha-enamidonitriles is evaluated through the synthesis of original heterocycles.