Photoinduced Multicomponent Synthesis of alpha-Silyloxy Acrylamides, an Unexplored Class of Silyl Enol Ethers

摘要

The photoinduced, multicomponent reaction of alpha-diazoketones, silanols, and isocyanides affords alpha-silyloxy acrylamides, formally derived from alpha-keto amides. The presence of a secondary amido group makes classic preparative methods for silyl enol ethers unfeasible in this case, while the mild conditions required by this photochemical approach allow their synthesis in good yields; moreover, the general structure can be easily modified by varying each component of the multicomponent reaction. Fine-tuning of the reaction conditions (i.e., solvents, radiation, additives) can be exploited to obtain complete Z selectivity. The reactivity of this overlooked class of silyl enol ethers has been investigated, and features that cloud pave the way to new applications have been found.