Synthesis of Functionalized Vinylsilanes via Metal-Free Dehydrogenative Silylation of Enamides.

A novel method of metal-free dehydrogenative silylation of enamides has been developed. The desired functionalized vinylsilane products were obtained in moderate to good yield and with high stereoselectivities. This protocol displays good tolerance of various functionalities. Furthermore, the high chemoselectivity of this reaction enables us to introduce different unsaturated C-C moieties to the products. The ease of further derivatization of the products to other useful compounds also demonstrates the highly synthetic utility of the current methodology.

Copper-catalyzed silylation reactions of propargyl epoxides: easy access to 2,3-allenols and stereodefined alkenes.

Efficient silylation reactions of propargyl epoxides catalyzed by copper catalysts have been developed. Under mild reaction conditions, tri- and tetra-substituted functionalized allenols and alkenes could be selectively obtained in moderate to high yields via tuning the bases and solvents used in the reactions. This work provides straightforward and efficient approaches to the synthesis of multifunctionalized 2,3-allenols and stereodefined alkenes from the same starting material of propargyl epoxides.