He, Yuan; Lou, Jiang; Wu, Kaikai; Wang, Hongmei; Yu, Zhengkun published the artcile< Copper-Catalyzed Radical C-C Bond Cleavage and [4+1] Annulation Cascade of Cycloketone Oxime Esters with Enaminothiones>, Application In Synthesis of 112-63-0, the main research area is thiophene cyanoalkyl amino derivative synthesis; ring cleavage annulation cascade cycloketone oxime ester enamino thione; copper catalyzed radical carbon carbon bond cleavage annulation cascade.
Carbon-carbon bond formation is among the most important reactions in organic synthesis. Reconstruction of a carbon-carbon bond through ring-opening C-C bond cleavage of a strained carbocycle usually occurs via a thermodynamically preferable pathway. However, carbon-carbon bond formation through thermodynamically less favorable C-C bond cleavage has seldom been documented. Herein, we disclose an unusual C-C bond cleavage of cycloketone oxime esters for [4+1] annulation. Under anaerobic copper(I) catalysis, cycloketone oxime esters underwent regioselective, thermodynamically less favorable radical C-C bond cleavage followed by annulation with enaminothiones; i.e., α-thioxo ketene N,S-acetals efficiently affording 2-cyanoalkyl-aminothiophene derivatives Cyclobutanone, -pentanone, -hexanone, and -heptanone oxime esters could act as the effective C1 building blocks in the annulation reaction. An iminyl radical mechanism is proposed for the rare C-C bond cleavage/[4+1] annulation cascade.
Journal of Organic Chemistry published new progress about [4+1] Cycloaddition reaction. 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, Application In Synthesis of 112-63-0.
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics