Synthesis of 1,3-Dicarbonyl Compounds using N-Cbz Amides as an Acyl Source under Transition-metal-free Conditions at Room Temperature

A wide range of functionalized N-Cbz amides underwent base-promoted C-C coupling reactions with enolizable esters, ketones and amides to afford 1,3-dicarbonyl compounds under mild conditions. The reactions proceeded at room temperature in the presence of LiHMDS in cyclopentyl methyl ether (CPME). The desired beta-ketoesters, beta-keto amides and 1,3-diketones were obtained in good to excellent yields in a short reaction time. Broad substrate scope, functional group tolerance and metal-free conditions are the merits of the developed methodology.

Automated summary

A developed method for C-C coupling reactions allows a wide range of functionalized N-Cbz amides to react with enolizable esters, ketones, and amides to produce 1,3-dicarbonyl compounds under mild conditions. The reactions proceed at room temperature in the presence of LiHMDS in CPME, resulting in good to excellent yields of desired products in a short reaction time.