Copper(I)-Catalyzed [4+2] Oxidative Annulation of α,β-Unsaturated Ketoxime Acetates with Cyclopropanols toward Functional Pyridines

A Cu(I)-catalyzed [4+2] oxidative annulation of alpha,beta-unsaturated ketoxime acetates with cyclopropanols has been developed for the synthesis of 2,4,5-trisubstituted pyridines in 28-76% yields. This method employs cyclopropanols as C2 synthons and features various functional group compatibility and gram-scale synthesis. In addition, a plausible reaction pathway was proposed based on the mechanism studies.

Automated summary

A Cu(I)-catalyzed [4+2] oxidative annulation reaction between alpha,beta-unsaturated ketoxime acetates and cyclopropanols has been developed for the efficient synthesis of 2,4,5-trisubstituted pyridines in good to moderate yields (28-76%). This method utilizes cyclopropanols as C2 synthons and demonstrates excellent functional group compatibility and scalability. Mechanistic studies support a plausible reaction pathway.