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

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...

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Bibliographic Details
Published in:Organic letters 2023-02, Vol.25 (6), p.1020-1024
Main Authors: Yepes, Paz, Suárez-Sobrino, Ángel L., Rodríguez, Miguel A., Ballesteros, Alfredo
Format: Article
Language:English
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Letter
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c00221