Synthesis of (E)-,-Unsaturated Carbonyls via Silver-Catalyzed Tandem Epoxide Rearrangement/Intermolecular Carbonyl- Heteroalkyne Metathesis

摘要

A regio- and stereoselective method for the synthesis of (E)-,-unsaturated carbonyls has been developed via a silver-catalyzed tandem epoxide rearrangement/intermolecular carbonyl-heteroalkyne metathesis. Various heteroalkynes including ynol ethers, ynamides, and thioalkynes work well for this transformation, leading to the production of (E)-,-unsaturated esters, amides, and thioesters in moderate to excellent yields with good functional group compatibility. It represents one of the rare examples of regio- and stereoselective intermolecular alkyne-carbonyl metathesis (ACM).