The alkylation of silyl enol ethers with SN 1-unreactive iodides in the presence of silver trifluoroacetate
CW Jefford, AW Sledeski, L Patrick, J Boukouvalas
Index: Jefford, Charles W.; Sledeski, Adam W.; Lelandais, Patrick; Boukouvalas, John Tetrahedron Letters, 1992 , vol. 33, # 14 p. 1855 - 1858
Full Text: HTML
Citation Number: 23
Abstract
General procedure: The silyl enol ether (2 mmol) and alkyl halide (2.1 mmol) are successively added to a suspension of AgOCOCF 3 (2.1 mmol) in dry CH 2 Cl 2 (2 ml) with stirring under argon at −70 to 25°C (see Table). The reaction is usually complete after 10 min at 25°C. Finally, the mixture is filtered over celite.
Related Articles:
Catalytic Deprotection of Acetals in Basic Solution with a Self??Assembled Supramolecular “Nanozyme”
[Pluth, Michael D.; Bergman, Robert G.; Raymond, Kenneth N. Angewandte Chemie - International Edition, 2007 , vol. 46, # 45 p. 8587 - 8589]
Oxidative Cleavage of Oximes with Silica??Gel??Supported Chromic Acid in Nonaqueous Media
[Ali, Mohammed Hashmat; Greene, Stacie; Wiggin, Candace J.; Khan, Saira Synthetic Communications, 2006 , vol. 36, # 12 p. 1761 - 1767]
[Shimizu, Isao; Tsuji, Jiro Journal of the American Chemical Society, 1982 , vol. 104, # 21 p. 5844 - 5846]
A convenient palladium-catalyzed aerobic oxidation of alcohols at room temperature
[Schultz, Mitchell J.; Park, Candice C.; Sigman, Matthew S. Chemical Communications, 2002 , # 24 p. 3034 - 3035]
[Lenze, Matthew; Sedinkin, Sergey L.; Bauer, Eike B. Journal of Molecular Catalysis A: Chemical, 2013 , vol. 373, p. 161 - 171]