Silylium-Catalyzed Regio- and Stereoselective Carbosilylation of Ynamides with Allylic Trimethylsilanes.

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.

SUBMITTER: Yepes P 

PROVIDER: S-EPMC9942199 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature