Nickel-Catalyzed Stereoselective Synthesis of Z-Enol Silanes

Significance

A novel three-component coupling of enals, alkynes, and silanes is achieved under nickel-catalyzed conditions. The reaction is highly selective for the Z-isomer and highly functional-group tolerant, giving a broad scope for each component. In some cases, in situ formation of the aldehyde occurs due to the instability of the corresponding silyl enol ethers. However, most products are functionalized silanes that can be used for further transformations such as Mukai­yama aldol reactions.