DOI
10.1055/a-1959-2505
Abstract
Ketones and related substrate classes undergo enol silane formation in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and triethylamine, reaction conditions that also promote the in situ ionization of allyl propionates. When these two processes are performed in one pot, allylation of the ketone is observed in high yields. Aldehydes, esters, and thioesters also serve as enol silane precursors under these conditions. When unsymmetrical allyl cations are employed, regioselectivity depends upon the electronic and steric properties of the substituents.
Document Type
Article
Publication Date
2023
Publisher Statement
© 2024 Georg Thieme Verlag KG
SYNTHESIS is an international, single-anonymized peer-reviewed, full-paper journal devoted to the advancement of the science of chemical synthesis. It covers all fields of organic chemistry involving synthesis, including catalysis, organometallic, medicinal, biological, and photochemistry, but also related disciplines. SYNTHESIS provides dependable research results with detailed and reliable experimental procedures and full characterization of all important new products as well as scientific primary data.
Recommended Citation
Heafner, E. D., Lin, X., Connors, A. H., Zhong, H., Coyle, R. J., Liu, Y., & Downey, C. W. (2023). One-pot enol silane formation-allylation of ketones promoted by trimethylsilyl trifluoromethanesulfonate. Synthesis, 55. https://doi.org/10.1055/a-1959-2505