Cesium Carbonate Catalyzed Oxa-Michael Addition of Oximes to Acrylonitrile

We report the O-alkylation of oximes with Michael acceptors using Cs2CO3 as the catalyst. The transformation proceeds stereospecifically with retention of the oxime configuration. Irradiation with visible light in the presence of diphenyl anthracene and cerium complexes affects the E to Z configuration ratio of the oxime ether products, but a complete stereocontrol was not achieved. The operationally simple protocol allows the synthesis of various O-alkylated oxime products that are useful precursors for further chemical transformations.

Automated summary

Researchers reported the O-alkylation of oximes with Michael acceptors using Cs2CO3 as the catalyst, achieving stereospecific transformation with retention of oxime configuration. Irradiation with visible light in the presence of diphenyl anthracene and cerium complexes affected the E to Z configuration ratio of the oxime ether products, but complete stereocontrol was not achieved. The operationally simple protocol allows the synthesis of various O-alkylated oxime products useful as precursors for further chemical transformations.