One-pot silyl imidate formation-N-alkylation reactions of amides with propargyl propionates

Authors

Tyler G. Chong
Alex V. Helbling
Remi D. Graff
C. Wade Downey, University of RichmondFollow

DOI

10.1016/j.tetlet.2023.154718

Abstract

The combination of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and i-Pr2NEt promotes the N-alkylation of primary and secondary amides with propargyl propionates. The amide substrates are believed to undergo conversion to nucleophilic silyl imidates in the presence of TMSOTf and the amine base, conditions which also promote propargyl cation formation in the same flask through the loss of trimethylsilyl propionate, leading to N-propargylation of the amide. A range of amides and propargyl propionates react efficiently in this reliable one-pot process with yields ranging from 19 to 99%.

Document Type

Article

Publication Date

8-22-2023

Publisher Statement

© 2023 Elsevier Ltd. All rights reserved.

Recommended Citation

Chong, T. G., Helbling, A. V., Graff, R. D., & Downey, C. W. (2023). One-pot silyl imidate formation-N-alkylation reactions of amides with propargyl propionates. Tetrahedron Letters, 128. https://doi.org/10.1016/j.tetlet.2023.154718