Silylium-Catalyzed Regio- and Stereoselective Carbosilylation of Ynamides with Allylic Trimethylsilanes
Organic letters(2023)
Abstract
The regio- and stereoselective carbosilylation of tosylynamides with allylic trimethylsilanes takes place under mild conditions in the presence of catalytic TMSNTf2 or HNTf2 to give (Z)-α-allyl-β-trimethylsilylenamides with good yields. Theoretical calculations show the activation of the C-C triple bond of the ynamides by the trimethylsilylium ion and formation of a β-trimethylsilylketenimonium cation. Further transformations of the products demonstrate the synthetic utility of this reaction.
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